40936-70-7

Upstream product

• 108-98-5 thiophenol 
• 4285-42-1 N-phenyl-N-methylcarbamoyl chloride 
• 882-33-7 diphenyldisulfane 
• 36602-08-1 (N-methylanilino)acetonitrile 
• 100-61-8 N-methylaniline 
• 92289-43-5 imidazole-1-carboxylic acid methylphenylamide 
• 132431-15-3 2-(N-methylanilino)-2-phenylsulfanylacetonitrile 
• 13464-19-2 phenyl chlorothioformate 

Relevant academic research and scientific papers

Palladium-catalyzed insertion reactions of isocyanides into thiocarbamates and selenocarbamates

The insertion reaction of isocyanides with thiocarbamates and selenocarbamates in the presence of a Pd(0) catalyst to selectively give 2-oxoethanimidothioates and -selenoates is reported. This is the first example of the insertion of an isocyanide into a

Carbamoylimidazolium and thiocarbamoylimidazolium salts: Novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides

Carbamoylimidazolium salts act as efficient N,N-disubstituted carbamoylating reagents. These salts are readily prepared by the sequential treatment of secondary amines with N,N′-carbonyldiimidazole (CDI) and iodomethane. The carbamoylimidazolium salts are more efficient carbamoyl transfer reagents than the intermediate carbamoylimidazoles, as a result of the 'imidazolium' effect. Kinetic studies on the base promoted hydrolysis of both carbamoylimidazoles and carbamoylimidazolium salts reveal over a hundred-fold rate acceleration. The salts react with amines, thiols, phenols/alcohols, and carboxylic acids in high yields, without the need for subsequent chromatographic purification of the products, producing ureas, thiocarbamates, carbamates, and amides, respectively. Analogous thiocarbamoylimidazolium salts were also synthesized from secondary amines and N,N′-thiocarbonyldiimidazole (TCDI), followed by methylation with iodomethane.

A new protocol for the formation of carbamates and thiocarbamates using carbamoyl imidazolium salts

Carbamoyl imidazolium salts are demonstrated to act as useful carbamoylation reagents, in reactions with alcohols, phenols, thiols and thiophenols to form carbamates and thiocarbamates under relatively mild conditions. The salts are stable and easily prepared from the corresponding amines using CDI.

2-(N-Methylanilino)-2-phenylsulfanylacetonitrile, A Reagent Tested for Electrophilic, Nucleophilic, and Radical Reactions

2-(N-Methylanilino)-2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide.Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated α-aminoalkenenitriles of 2E-configuration.Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates.Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by CuI or Lewis acids to give varied α-amino nitriles.The 4-oxo-2-aminonitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung.When 1 was treated with tributylstannane, the corresponding amino nitrile α-radical was formed and the self-coupling product was isolated.