30085-50-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 6867, 1991 DOI: 10.1016/0040-4039(91)80428-9

Upstream product

• 88-10-8 N,N-diethylcarbamyl chloride 
• 100-53-8 phenylmethanethiol 
• 21055-93-6 sodium salt of diethylthiocarbamic acid 
• 100-44-7 benzyl chloride 
• 2430-00-4 2,2,2-trichloro-N,N-diethylacetamide 
• 6258-66-8 (4-chlorophenyl)methanethiol 
• 150-60-7 dibenzyl disulphide 
• 617-84-5 N-formyldiethylamine 
• 16601-01-7 benzenethiosulfonic acid S-benzyl ester 
• 3052-61-7 N,N-diethylaminodithiocarboxylic acid benzyl ester 
• 201230-82-2 carbon monoxide 
• 109-89-7 diethylamine 
• 100-39-0 benzyl bromide 
• 34879-74-8 1-diethylaminyl benzyl sulfide 

Relevant academic research and scientific papers

Visible-light-promoted synthesis of secondary and tertiary thiocarbamates from thiosulfonates andN-substituted formamides

A general visible-light-promoted metal-free synthesis of secondary and tertiary thiocarbamates starting from thiosulfonates andN-substituted formamides is developed. By employing rhodamine B as a photocatalyst andtert-butyl hydroperoxide (TBHP) as an oxidant, a wide scope of thiocarbamates can be obtained through direct thiolation of acyl C-H bonds under irradiation of blue light at room temperature for 12 h.

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).

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.

Synthesis of S-alkyl and S-aryl thiocarbamates, one-pot two-step general synthesis

A method for preparing S-alkyl and S-aryl thiocarbamates comprising reacting a precursor thiol reagent with trichloroacetyl chloride to produce an S-alkyl and S-aryl trichloroacetyl thioester intermediate, which is reacted with an amine to yield the corre

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.

Oxidation of dithiocarbamates and synthesis of a stable sulfine

Investigation of the oxidation reaction of various dithiocarbamates demonstrated that the corresponding sulfines (S-oxides) are formed. Though their stabilities are very moderate, a number of sulfines could be isolated and characterised. When left at ambient temperature they decomposed to thiolocarbamates and dithiocarbamates. The sulfines from secondary dithiocarbamates led to disulfides which formation was explained. With a sterically hindered aryl group present on the sulfur atom, a stable sulfine was prepared and its crystal structure was analysed.

Rice field surface microlayers: Collection, composition and pesticide enrichment

The thin organic film (surface microlayer) found on natural waters can concentrate hydrophobic pollutants. Enrichment factors (EFs), the ratio of pollutant concentration in microlayer to that in subsurface water, previously have been measured in relativel

Reaction of Thiolates with Carbon Monoxide

Thiolates generated from elemental sulfur with amines or lithium amides, easily reacted with carbon monoxide to form thiocarbamates in good yields.Furthermore, the reaction of diaminodisulfide with carbon monoxide in the presence of DBU proceeded similarl

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.