39078-72-3

Upstream product

• 75-18-3 dimethylsulfide 
• 75-05-8 acetonitrile 
• 624-92-0 Dimethyldisulphide 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 109-73-9 N-butylamine 
• 201230-82-2 carbon monoxide 
• 74-88-4 methyl iodide 

Downstream Products

• 1461-79-6 N-butylpiperidine-1-carboxamide 
• 2158-01-2 N-butyl-N'-cyclohexylurea 
• 3083-88-3 N-butyl-N'-phenylurea 
• 53693-74-6 3-butyl-1-methyl-1-phenylurea 
• 14117-22-7 N-benzyl-N′-butylurea 
• 3149-00-6 phenbutamide 
• 24535-66-8 N-butyl-N'-(o-tolylsulfonyl)urea 
• 592-31-4 1-butyl-urea 
• 41891-17-2 N-butylcarbamoyl chloride 
• 76114-73-3 butylcarbamic acid prop-2-ynyl ester 
• 64-77-7 N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide 
• 19035-01-9 1-Butyl-3-(1-phenyl-ethyl)-urea 

Relevant academic research and scientific papers

Preparation of mono-, di-, and trisubstituted ureas by carbonylation of aliphatic amines with S,S-dimethyl dithiocarbonate

General procedures are reported to prepare N-alkylureas, N,N′-dialkylureas (both symmetrical and unsymmetrical), and N,N,N′-trialkylureas by carbonylation of aliphatic amines, employing S,S-dimethyl dithiocarbonate (DMDTC) as a phosgene substitute. All reactions were carried out in water. Symmetrical disubstituted ureas were prepared directly working at 60°C with a molar ratio of DMDTC:amine = 1:2, preferably under nitrogen. Unsymmetrical ureas were prepared in two steps via S-methyl N-alkyl-thiocarbamate intermediates, which are formed selectively in the first step at room temperature. These intermediates react in the second step with ammonia or various aliphatic amines, both primary and secondary, at temperatures varying between 50 and 70°C. All the target ureas were obtained in high yields (28 examples, average yield 94%) and with very high purity (generally >99.2%). Also to be noted is the recovery of a co-product of industrial interest, methanethiol, in an amount of two moles for each mole of DMDTC, with complete exploitation of the reagent. Georg Thieme Verlag Stuttgart.

Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions

DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20°C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbencarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H 2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20°C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

Synthesis of sulfonylurea derivatives used as oral antidiabetics by the selenium-assisted carbonylation using carbon monoxide with sulfur

Sulfonylurea derivatives including useful antidiabetics (Tolbutamide, Chlorpropamide) were synthesized in good yields from benzene-sulfonamides with thiocarbamates in the presence of DBU. Thiocarbamates were prepared by the selenium-assisted carbonylation

Synthesizing thiocarbamic acid esters

A process for the synthesis of thiocarbamic acid esters by reacting amine compounds having a general formula STR1 wherein A is an arylene radical, simple or substituted by halogens hydrocarbon radicals, alkoxy groups, or can be an alkylene radical having