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Usage

InChI:InChI=1/C9H19NOS/c1-5-8(4)11-9(12)10(6-2)7-3/h8H,5-7H2,1-4H3

Upstream product

• 542-69-8 1-iodo-butane 
• 22318-01-0 diethylamonium N,N'-dimethylmonothiocarbamate 
• 201230-82-2 carbon monoxide 
• 109-89-7 diethylamine 
• 629-45-8 dibutyl disulfide 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 23870-65-7 S-butyl-N,N-diethyl-thiohydroxylamine 
• 13889-94-6 butyl chlorothioformate 

Relevant academic research and scientific papers

A facile method for the synthesis of thiocarbamates: Palladium-catalyzed reaction of disulfide, amine, and carbon monoxide

(Equation Presented) A new method for the synthesis of thiocarbamates has been developed. When dialkyl or diaryl disulfides were allowed to react with secondary amines and carbon monoxide in the presence of a catalytic amount of a palladium complex, the thiocarbamates were obtained in moderate to good yields. In contrast to that of secondary amines, in the reaction of a primary amine, no formation of thiocarbamate was confirmed, but urea was formed in good yield.

Palladium-catalyzed azathiolation of carbon monoxide

A novel palladium-catalyzed azathiolation of carbon monoxide using sulfenamide (RSNR'2) (1) is described to provide thiocarbamate 2 in good yields. The mechanistic proposal includes the following: (1) insertion of CO into Pd-S bond of Pd(SR)2(PPh3)(n) 4 to provide Pd[C(O)SR](SR)(PPh3)(n) 5 and (2) σ-bond metathesis between S-N and Pd-C(O) bonds to afford 2 with the regeneration of 4.

Novel synthesis of S-alkyl thiocarbamates from amines, carbon monoxide, elemental sulfur, and alkyl halides in the presence of a selenium catalyst

Carbonyl selenide easily reacted with elemental sulfur at low temperature to form carbonyl sulfide in a good yield, and reaction of ammonium salts of selenocarbamates with elemental sulfur brought about ready transformation to those of thiocarbamates. On the basis of the high catalytic activity of selenium for carbonylation of amines with carbon monoxide in addition to these important findings, a convenient new method for synthesis of S-alkyl thiocarbamates was developed through the carbonylation of amines with carbon monoxide and elemental sulfur in the presence of a selenium catalyst under mild conditions followed by alkylation of ammonium salts of the thiocarbamates with alkyl halides.

REACTIONS OF UNSTABLE DIALKYLCARBAMOYL LITHIUMS WITH SULFUR COMPOUNDS

Unstable dialkylcarbamoyl lithiums, generated from the reaction of lithium dialkylamides with carbon monoxide, were successfully trapped by sulfur compounds (elemental sulfur, disulfides, carbon disulfide, and carbonyl sulfide) at low temperature, through their potent affinity with a sulfur atom.These efficient reactions were also applied to development of a facile synthetic method for thiocarbamates, useful herbicides, and thiooxamates.

Facile synthesis of S-alkyl thiocarbamates through reaction of carbamoyl lithium with elemental sulfur

Efficient synthesis of S-alkyl thiocarbamates was developed. The key step of this synthetic method is a conversion of carbamoyl lithium, generated from lithium dialkylamide and carbon monoxide, to lithium thiocarbamate by addition of elemental sulfur.