Questions related to Synthetic Chemistry
I was wondering if I would need to break the disulfide in my compound and then protect the thiols before performing michael addition reaction on primary and seconadry amines?
Planning on doing the reaction at 90-95C for 3 days, no solvent
I want to synthesize the amide functionalised diamine in the image which I have attached. The image shows the route I am considering, but I was wondering if any of the synthetic chemists out there could be of assistance? Is there an alternative approach to making this compound? One that still relies on readily available materials and potential has fewer steps or is more economical in any way.
Any assistance on this would be appreciated.
I am trying to synthesise FeBr2THF2 from FeBr2 and THF but the reaction doesn't seem to work for me.
FeBr2 is stored in a glove box, THF is dried over sodium and benzophenone and the extraction carried out under an inert atmosphere. Conditions i use are 25g of iron bromide and about 150-160ml of THF refluxing for about 8hrs. I never observe white crystals as reported in literature. They didn't say how much THF they use although they used 100g FeBr2 for 12hrs reaction. I am limited to about 100ml of THF due to Soxhlet extractor size. If you have any hints or tips please share.
I made several reactions with 3,5-Dinitrobenzoyl chloride. When I looked at similar reactions for this substance, no heat was ever given in the reaction (even though heat increases the yield).
The interesting thing is that this substance turns black as soon as the heat is given to the reaction environment. Due to the fact that, theoretically, the polymerization of this material is impossible. Do you know the reason why they do not give heat to this material?
I prepared stock AdipoRon at 100 mg/ml in DMSO. It is a clear solution. However, I further dilute it to 10mg/ml working conc. with 0.85% NSS and get final 5% DMSO conc. It has become insolubility and precipitates around my 1.5 ml tube. I try to solve this by vortexing, pipetting, and incubating at 37'C but it doesn't work. So, I want to know" what is the solvent that use for preparation of working AdipoRon for in vivo exp.?
I am setting up an esterification reaction using EDC/DMAP for R-OH and R'-COOH conjugation in water. However, one of my reactants R' also has an amine (-NH2) group. I am curious as to how the reaction would proceed with EDC and DMAP? And the conjugation would be between R-OH and R'-COOH, and not between R'-COOH and R'-NH2.
Thanks in advance,
I'm trying to predict the retrosynthesis of an experimental compound from its SMILE string and 3D structure using IBM RXN Chemistry Server. I got some results but not sure about their reliability.
What are the other tools/software/servers available for computational predication of chemical synthesis of a particular compound? Need some methodical answers preferably from an expert of synthetic chemistry.
I am looking for a software that can predict the chemical reactions that will occur when I mix certain substances. For Example: Na+Cl --> NaCl.
I've attached a picture of manually drawn organic compound using "Pubchem Sketcher". I was planning to synthesis this molecule using synthetic chemistry protocols.
Considering me as a fresher to synthetic organic chemistry, I'd like to learn more about the following questions.
1. What are all the different synthetic routes/steps that could be used to synthesis this compound?
2. How do I find the chemicals list, the steps involved, and the reaction environment required for this compound synthesis?
3. What are all the computational tools to predict the organic synthesis pathways?
If organic synthesis protocols for this substructure is available, please share them for references.
Hari Prasath Nagaiah,
Let me preface this question by saying that this is all being done under a legal THC/Hemp license in the state of Colorado.
I was hoping to get some advice on how to improve my method for converting CBD into THC. Currently we have been attempting two methods.
Combine CBD isolate (99%) with ethanol at a 10:1 ratio. Add 2.42g of p-TSA for every 100g of CBD isolate added. Reflux at 63C for 47min. Following the reflux we do a bicarbonate wash to neutralize the pH followed by an extraction of the cannabinoids into an organic layer (Hexane) by titrating water into the solution. After separating the phases we evaporate the Hexane out of the organic layer and distill the remaining oil using short path distillation.
The purity tested by HPLC is approximately 50% Delta-8 THC and 15% Delta 9 THC. Following this reaction the end product is prepared for oxidative degydrogenation to form CBN. The higher the purity of Total THC prior to this reaction, the higher the purity of our CBN. This we are looking to make improvements to our methodology.
Points or potential improvement:
1.) commence reaction under a nitrogen atmosphere
2.) use 200 proof ethanol (currently using 190 proof)
3.) change reaction solvent to toluene/heptane
First dry your clay in a vacuum oven at 80C with a vacuum applied for 1Hr. Then combine CBD isolate with T-5 acid washed clay with 16% T-5 by weight (150g T-5 for 1000g CBD isolate). Reflux at 180C for 3Hr. Following the reflux distill using short path distillation.
This method has yielded us ~60% total THC. I’m not sure what improvements I could make on this methodology are.
Thank you all for any advice and insights you may have.
I've just tried to prepare several tertiary alcohol from benzoate with Grignard reagent. And I noticed that those benzoate bearing an unsubstituted amine show great difference in yield when amine group was on different site.(4 equiv. of EtMgBr added into a solution of aminobenzoate in anhydrous THF at -70oC or 0oC )
2-aminobenzoate gives excellent yield(>90% in most cases) but 3-aminobenzoate gives poor yield(less than 20% or even messy). Only those protected or substituted 3-aminobenzoate worked efficiently with Grignard reagent.
Is there any literature explaining this difference? Or someone is interested by this phenomenon?
I want to try this algorithm, but can't find a downloadable link or any data regarding its access and usage conditions, any help would be appreciated.
Au(III)Cl3 + Ag(I)TFSI in methanol -> Au(III)TFSI3 + AgCl (s)
and then, I will remove AgCl precipitates by filtration..
If this is impossible, what solvent or what method should I use?
(because HAuCl4 can be produced, water cannot be used, maybe)
Example: 3-acetyl-5-carbamoylsalicylic acid (OH, COOH, COCH3 and CONH2)
Likewise, how many different combinations are possible? Can it be penta/hexa-substituted? Exclude simpler functional groups like alkyls and halogens
Hi all, I need to cleave the ester in Ethyl 2-amino-1H-imidazole-5-carboxylate to make the carboxylic acid and retrieve the product from solution to use in downstream applications of linking to amines via reductive amination using sodium cyanoborohydrde.
I tried to cleave the ester with 2M equivalents of KOH in 5:1 MeOH:H2O for 1H at 40C. After 1H, i added 20mL H2O to quench and then tried to precipitate my newly made acid by dropping pH to 1, however nothing precipitated out. I then tried to see if any of my product was unreacted by mixing with diethyl ether to see if any of the light brown color would transfer to the ether layer, but again, nothing happened, the ether layer is completely clear. I guess I should just boil off some water and see if it starts to precipitate out? Im not much of a chemist so I just wanted to make sure I havent made any terrible assumptions along the way...
The background of this is lengthy, but in short, I am an experienced chemist with essentially no experience doing Grignard reactions.
Most recent literature uses mmol scales @ 0.1-1M concentrations. I need to run a ~1mol reaction, but multi-liter is out of the question. Small scale tests showed that concentrated solutions - but still with several equivalents of Mg-coordinating ether - were *extremely* viscous. No crystals or precipitation, but gelatinous to the point of not stirring. The reactions did not proceed as expected.
Very old mole scale literature usually uses Et2O.
Can someone with first hand experience on preparative scale Grignard rxns give me a feel for the maximum concentration of PhMgCl I should make from Mg/PhCl in THF?
I may need to run the reaction in several batches depending on the answer.
I am working with purification of gels, by washing with some solvents, so that, impurities get removed. But while doing that, I am getting some cracks after washing. I have fabricated gels by using polyesters using a bifunctional crosslinker, and I got a network also through esterification reaction. I used here EDC and DMAP as catalysts. I have used various solvents, like DMF, DMSO, Water, Chloroform for washing. but it didnot work. Could somebody share any idea to avoid this problem?
I'm trying to react Ar-CL compound (200mg) with a primary amine (1.2 equivalent), and I've found in the literature that they're using a very low amount of solvents (like 0.5ml) to proceed the Ullman coupling; how could this amount dissolve the reactants and the catalysts?
In fact, there're a lot of reactions I've seen being proceeded in a very low amount of solvent, but when I do them in the lab, I use something like 10x of the amount of solvent used in literature as I "feel' that the amount used in literature is very low to dissolve the reactants and the catalysts.
How bad could this affect the rate and the efficiency of the reaction?
Column chromatography with Silica Gel columns with inbuilt UV detector.
Compound structure is mainly poly unsaturated fatty acids and analogs without UV handles.
My di-phosphate salt compound contains two 3ry amino groups involved in salt formation and a one 2ry amine group that's not involved in salt formation. I wanna proceed N-Boc protection for this 2ry amino group; I'll proceed the reaction in water without using any bases.
Should I convert my compound to freebase first? or can I proceed it while in the salt form?
I am running a Steglich Esterification with EDC/DMAP in CH2Cl2 on a with the carboxylic acid being a potassium salt that is p-sulfonated. Will the sulfonate group be effected by this reaction? I plan to extract by washing the reaction with brine solution to remove excess EDC/DMAP - does this seem plausible? I do not want to acidify the reaction.
Hello all, I was try to evaluate the antioxidant activity of some synthesized compounds. So,I prepared an ethanol DPPH solution with a [ DPPH]= 60 uM (2.3 mg in 100 mL of absolute ethanol) but when I measured the absorbance at 517 nm.
Firstly, I found an absorbance value of 0.214 which is in contradiction with the literature (~0.6 for this concentration)
Secondly,for the same concentration ([ DPPH]= 60 uM ), I found an absorbance value of 0.214 when I worked in the range 600-400nm and a value of 0.340 when I worked in the range 800-400nm.
Please some one can help me to solve these problems?
The idea is to use base to create an anhydrous strong nucleophile, which needs to be as anhydrous as possible. Also the nucleophile should act as a sigma donor and not pi. Any leads is much welcome
how to stabilize the intermediate forms during inter conversion of one form the other?
is there any possibility of synthesizing the intermediates?
I am trying to synthesize boronic acid pinacol ester derivatives from aryl/hetero-aryl halides.
Is there any TLC staining technique which can indicate the formation of boronic acid?
My ammine part is only dissolved in DMSO and Aldehyde is dissolved in acetone, chloroform, methanol and others. What solvent should I use to form my desired imine? Can I use DMSO? WIll that may make any problem?
I would like to request the Researchers to let me know any procedures or references to carryout synthesis of Schiff bases of 4-Aminosalicylic acid when treated with different substituted benzaldehydes, which results in good yields and requires simple work-up (high atom efficient other than Ultrasound technique or Microwave)
I’m trying to couple a perylene derivative with borate using Suzuki-Miyaura coupling reaction. (Please see the attached file for the structure of the compound and the reaction conditions) Several compounds of similar structure were already synthesized using Pd(PPd3)4 in THF/Water. However, the reaction doesn’t proceed for the structure presented in the file. How can the synthesis of this compound using SM coupling reaction?
It looks like the MC3T3 may produce as high, or higher ALP, without ascorbic acid, and this seems counter intuitive. Has anyone else seen this, or noticed it in the literature? Every study I have read used ascorbic acid, so I haven't found anything published on this yet. If MC's produce ALP then is the addition of ascorbic really stimulating ALP production from differentiation?
Alexa Fluor 488 dyes are disulfonated analogs of Carboxyrhodamine 110. I have a protocol from a patent by Haugland. Has anyone tried synthesising this via some other method?
I am using pure organic compound with good thermal stability and it is practically insoluble in most of the solvents as catalyst for C-C bond formation. I want to determine its nature in catalysis.
1. I am performing reaction in neat cionditions (without solvent) at 100 C temperature, at this I think some of the catalyst is soluble but I can see most of the catalyst solid present in the mixture.
2. som example reactions due occur at room temp where catalyst is completely insoluble
3. without catalyst reaction won't go, increasing catalyst amount has positive effect. but overloading of catalyst reduced yield.
4. catalyst has amine and carbonyl groups at portals
5. Hot filtration method shows reaction stopped after removing catalyst by filtration.
Now kindly answer following queries,
1. How can I decide my catalyst is heterogeneous or homogeneous?
2. is there any specific test to conduct?
3. Is there any small organic compounds known to act as heterogeneous catalysts?
thank you for your interest and support
i want to prepare stable and pure phenylacetyl isothiocyanate from phenyl acetyl chloride. I tried the reaction with ammonium thiocyanate in solvent acetonitrile and toluene. But I am getting highly impure dark brown color oil.
I am using EDC as catalyst with polyesters having 4 free OH groups, to form gel network, by adding a crosslinker. Problem, I am facing is, that when I add EDC.HCl, it forms a network prior to adding crosslinker. Normal case is, it should form network after addition of crosslinker and not EDC. Could some one share his experience or suggest something about this problem?
I want to graft PBA (Phenyl boronic acid) with some polymer having pendant hydroxyl groups. From Previous literature and my own observation, boronic acid forms a complex with these polyols and forms a gel. I want to fabricate a gel system through chemical crosslinking at the end by adding a crosslinker, but i get a gel due to this complex prior to chemical crosslinking. Could somebody please suggest or share his experience that how can this complex formation b/w boronic and hydroxyls be overcomed?
I have a question related to the swelling property of a gel. If the main polymer backbone has got hydrophobic character but the crosslinker has got hydrophilic property. Will it affect its swelling property in water? If yes, then, To what extent, Will it affect? Also please share any experience to impart hydrophilic character to gel through crosslinker?
We suppose that an activity aimed at the solution of this problem should be developed not only because of population upsurge but also in view of creation of underground civilization due to the possible future natural events incompatible with the comfort life on the Earth’ surface. We propose the Life Origination Hydrate Theory (LOH-Theory) as the theoretical basis of such an activity.
Plants, basing on minerals, create primary food substances, and animals, basing on these primary food substances, create secondary food substances for mankind. This work is being performed on the basis of quite definite chemical processes and is being governed by universal physical laws and chemical regulations.
I am presently using diethanolamine in water at pH 7.8-8.8 at 75C requiring about 12hrs to complete the hydrolysis. This will be used for commercial production so large scale procedure is needed.
Possibly a catalyst on a solid support that is commercially available.
I have already found some information about my question on this site - https://www.gas-find.com/cyanure-de-potassium.html
And also the corresponding product - http://www.seton.co.uk/honeywell-plastic-rd40-filters.html#10CQF001
So I need to be sure, that I have chosen the right one.
I'm trying to deprotect hexylamine protected with -Tos group, just to see if the reaction with SmI2/amine/H2O (said to be instantaneous) works.
I prepared the solution of samarium iodide, SmI2, (1,2,-diiodoethane and Sm in THF) and I get the blue dark color. I tried the reaction with Et3N as the amine, and when I ad this final reagent to the reaction mixture I get the color change as the articles say it woul do. However I can't deprotect my amine group. Any help?
Does anyone have experience working with trimethylsilyl protected alkynes? I am wondering about their stability towards acids and bases.
Are they similar to silylethers?
I am trying to lithiate my compound(DTP) with TMEDA and BuLi(6 eq) for 1hr reflux(@ 80 degrees). It seems to be ineffective. Hence, I would like to know whether any other lithiated agent is there which serves my need?
I am synthesising N-(Benzyloxycarbonyl)-L-serine benzyl ester starting from N-(benzyloxycarbonyl)-L-serine by using benzyl bromide in aq. NaOH and Acetonitrile under reflux condition (by following a research article “Optimized synthesis of phosphatidylserine” By Guanti, Giuseppe et. al., From Amino Acids, 39(2), 367-373; 2010)
1) why no racemization was observed in such conditions?
2) If I run the reaction for whole night, is it possible to get racemization under such condition?
Exact procedure is N-(benzyloxycarbonyl)-L-serine (10.63 g, 44.4 mmol) was suspended in CH3CN (50 ml), and treated with 4 M aqueous NaOH (11.175 ml, 44.7 mmol). The resulting solution was treated with n-Bu4NHSO4 (1.52 g, 4.48 mmol) and BnBr (6.40 ml, 53.9 mmol) and refluxed for 4 h. After cooling to r.t. (a white solid separates), 5% aqueous NaHCO3 (55 ml) was added and the suspension stirred for 20 min. After removal of the solid through filtration, the two phases were separated and the aqueous one extracted three times with AcOEt (40 ml each). The reunited organic phases were washed with brine, well dried with Na2SO4 and evaporated to dryness to give an oil. It was taken up in n-hexane (40 ml) and stirred until a well solid separates. It was filtered on a Buchner filter and washed with n-hexane. Finally, the solid was crystallized from Et2O/PE to give pure N-(Benzyloxycarbonyl)-L-serine benzyl ester as white solid, yield (11.03 g, 75%). m.p. 81.9-82.6°C. Rf = 0.34 (PE/Et2O 3:7).
This was a mitsonubu reaction performed between N-methyl diethanolamine, N-hydroxypthalimide (NHP), PPh3, DIAD, THF at 0 degree celcius, and stirred for 12 hr at RT! Any ideas will be appreciated. Thanks.
I have solid powder of carboxy phthalocyanine (PcCOOH) and want to convert it to -COCl. So can solid sample be converted directly to COCl by adding SOCl2 and refluxing or I have to dissolve it in some solvent to achieve individual molecular entity in solution. I am afraid if SOCl2 can reach between the stacked phthlocyanine molecules in solid sample.
Thanks in advance
I am able to tosylate 2-iodoprop-2-enol easily (>80%) but with 2-(4-iodooxazol-2-yl)prop-2-enol there is no conversion using the same method (NEt3, NMe3*HCl, TsCl). Can anyone provide an explanation? I cannot understand, why the oxazole should make such a big difference.
I have also tried DMAP and DABCO, but no success.
Does anyone have a possible alternative to introduce an alkyne in place of the alcohol?
Thanks a lot in advance!
I have been trying to do a reaction of DSPE with NHS-PEG-NHBoc to make DSPE-PEG-NH-Boc. Maldi MASSS data looks like DSPE does not react with NHS. I checked temperature ,base . But still I have problem. Could you suggest me anything about reason? I saw couple of literature about it, increased temperature up to 50degree and used Base DIEA. I still did not get expected result. I need some suggestion from you guys if you have any idea. Thanks in advance.
I am currently trying to validate VOCs that are not present in the SIFT-MS compound library. The commercially available standard only exists as a mixture of stereo isomers (cis/trans). Before we try to isolate the isomers, which is time-consuming and still in need of a lot of experimentation, I was wondering if the different isomers can have different product ions or if it will just be the same product ions with different branching ratios?
I want to obtain a solid by precipitation. I used two antisolvents ( dietheyl ether and petroleum ether), after I put the mixture in fridge. I obtain after that kind of crytal shapes. I want to filtrate under vaccum to get pure crystals. HOEWEVER, after some time the crytals (solid) disappear! Any explanation to this phenomenon? and what should I do to keep my solid?
A compound I wish to synthesize requires a preliminary nitration step, and I have several questions about how to best do this with my available reagents, as well as general guidelines for doing these reactions.
Regarding the nitrating reagents, red or white fuming nitric acid is not available in our laboratory, and we only have access to 70% nitric acid, as well as KNO3, NaNO3 and NH4NO3
The only literature procedure available for this compound requires the use of fuming nitric acid, and acetic anhydride as solvent. I attempted it using our 70% solution and it gave very poor results. My aromatic system is moderately deactivated with no electron donating groups, and I suspect that the water in the 70% solution is problematic here.
Using the 70% solution, I am under the impression that with concentrated H2SO4 as solvent/acid/dehydrating agent, the mixture should be strong enough to allow the reaction to take place.
1) About how many molar equivalents of HNO3 would you generally add, and about how many milliliters of concentrated H2SO4 do these reactions require per milliliter of 70% HNO3 to get adequate dehydration? Just looking for a general range.
2) When quenching the reaction, about how many milliliters of ice water do you pour the reaction mixture into per milliliter of concentrated H2SO4? Again, I'm just looking for a general range.
Additionally I've seen a number of procedures for nitration using either KNO3, NaNO3 or NH4NO3, in conjunction with Concentrated H2SO4 to produce anhydrous nitric acid in situ.
3) Which of the Nitrate salts do you prefer/which have given you the best results?
4) Most procedures I've seen with the in situ generated HNO3 are as follows:
a) premix H2SO4 with 1.1 equivalents of the nitrate salt and add this solution to the substrate in H2SO4 at 0˚C,
b) portionwise add 1.1 equiv. of the solid Nitrate salt to the substrate in H2SO4 at 0˚C
c) Slurry the substrate in CH2Cl2 with 1.1 equivalents of the Nitrate salt at 0˚C, and then dropwise add H2SO4.
If you have done one of these, which ones worked well for you?
I attempted procedure "b" with NaNO3 but it seems to dissolve very very slowly in the H2SO4 solution at 0˚C, and is still pretty slow even at ambient temperature, and it seems likely I could get a large temperature spike on larger scales if the heat of the reaction rises too quickly causing the undissolved NaNO3 to dissolve and then react, making me hesitant about using this procedure.
5) For these reactions done in a chlorinated solvent with H2SO4, Will there be any issues with the slight (0.1 equiv.) excess of HNO3 / NO2+ reacting with the solvent that I need to worry about? Or is CH2Cl2 relatively inert under these conditions?
Thanks in advance!
How to prepare zinc carbonate ? is there any process for the separation of Zinc carbonate from Magnesium carbonate?
Hi, I have trouble cleaving off the phenyl glycinol chiral auxilliary from my amino acid analogue. I have only tried oxidative conditions, (PbOAc4) varying the reaction time, temperature and solvent. I am reluctant to use hydrogenolysis due to the fact that my molecule is labile in reductive conditions. Any suggestions?
i tried by this method
5-bromo pentanal & (4-Carboxybutyl)triphenylphosphonium bromide in presence of NaHMDS in THF SOLVENT , i got product but very low yield & HNMR shows desired compound signals along triphenyl phonium oxide , plz suggest best method
A similar reaction with a t-butyl substituent on the 2-position on the phenol is complete in 1 hour without a solvent at 105 degrees C. It also works by refluxing overnight in ethanol. These methods were tried but not successful. Reflux or heating for a longer time didn't work.
I am trying to attach N-Boc-3-bromopropylamine to both of the phenols of 7-hydroxycoumarin dimer with no success. I have tried K2CO3 in DMF at 80C, Cs2CO3 in DMF at 60C, TEA in DMF at 80C, DMAP in DMF at 80C & 110C but have not formed the desired product in any of these conditions and have seen significant side reactions. Does anyone know a set of conditions I should try (especially varying the solvent used as I have only used DMF)? I have attached the structure of the desired product.
i ran a pectet-spengler reaction using equimolar amounts of tryptamine hydrochloride and aldehyde refluxed in methanol with catalytic amount of acetic acid but even after 107 h, both reactants did not consume completely. reaction was also refluxed in acetic acid with TFA as a catalyst. i think it might be because tryptamine hydrochloride was present in salt form or due to schiff base which is intermediate. i plan to neutralize tryptamine hydrochloride and neede guidance. thanks
I've been having trouble trying to purify 3-methylnona-1,8-dien-3-ol from a grignard reaction utilizing vinylmagnesium bromide. There is a file attached the shows the synthetic scheme. I'm not completely sure what is going wrong, but I obtain about 6-7 spots on TLC after the reaction is quenched and worked up. Has anyone had trouble with side reactions during grignard and ketone reactions? Any advice helps! Thank you!
I came across this reaction in literature where they successfully reacted delta-valerolactone (5 membered ring) with LDA. I've tried the same reaction substituting this valerolactone with the PDL but with no success. Is omega-pentadecalactone lactone less reactive because it is bigger?
Will using NaNH2 instead of LDA be more effective?
All help is appreciated.
In desulfurization of fuel oils I found an article that explains the capacity of 1860 ionic liquids to Thiophene and Dibenzothiophene.
I would like to know how to carry out COSMO-RS Study ?
here the attached article
Desulfurization of Fuel Oil: Conductor-like Screening Model for Real Solvents Study on Capacity of Ionic Liquids for Thiophene and Dibenzothiophene
I ran a sephadex column with 50%CHCl3:MeOH solvent system. In first 10 vials, i got a mixture of compounds with tails (streakings) after i run the TLC. But i got 2 compounds in next vials. Should i run this mixture of compounds (present in first 10 vials) again in the sephadex lh-20 with same 50% CHCl3:MeOH or i should better use 100% MeOH solvent for its purification?