Does anyone know if thioamides are stable in alkaline media? If not, what are the expected degradation/reaction products?
In alkaline aqueous media very probably the thioamide will give the corresponding amide.
I thaught so. I know that they are less stable than amides, so I am trying to find a solvent that will not react with thioamides. Any suggestions? I suppose I can exclude all nucleophilic solvents?
Currently we are working with thioamides in the process of making enaminones. Thioamides are pretty stable in organic solvents. you can use dichloromethane, benzene, ethyl acetate. In fact we are using dichlorometane as a solvent in the synthesis of verity of thioamides.
Primary, Seconary thioamides in alakali media readily undergo deprotonation (even with Sodium bicarbonate) and end up with iminothiols.
Thank you for your input. I would like to use as polar of a solvent as possible. Did you maybe try using methanol or acetonitrile for your thioamides? Do you think that methanol would attack the electrophilic site at thioamide? Also, are thioamides stable in water? What about acidic aqueous conditions, do they hydrolize?
indeed, for a polar solvent , MeCN better than MeOH. See also this revue
MeOH could be really problematic, use isopropylalcohol. Normally ACN is not a problem.
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