2941-55-1Relevant academic research and scientific papers
New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water
Milosavljevic, Milutin M.,Mijin, Dusan Z.,Milisavljevic, Smiljka S.,Elezovic, Natasa M.,Milanovic, Jelena K.
, p. 1833 - 1837 (2014/01/06)
A simple and efficient one-pot synthesis was developed for the preparation of S-alkyl thiolcarbamates from xanthogenate without catalyst using water as a solvent. The water can be recycled after removal of the product. The significant features of this protocol are: operational simplicity, mild reaction conditions, recycling of solvent and high product yields. Starting basic alkyl xanthogenate reacts with alkyl ammonium sulfate (aryl ammonium sulfate) and hydrogen peroxide (molar ratio 1:0.55:1) in water at 40 C for 1 h, followed by additional heating at 70-110 C for 1-2.3 h. Good to excellent yields were achieved using ammonium sulfate in 10 % molar excess. Graphical abstract: [Figure not available: see fulltext.]
Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: a route to diversely substituted S-alkylcarbamothioates
Doukara, Abdallah Larbi,Mehdid, Mohammed Amine,Djafri, Ayada,Andreoli, Federico,Vanthuyne, Nicolas,Roussel, Christian
experimental part, p. 1852 - 1858 (2010/04/04)
A new route to S-alkylcarbamothioates is disclosed. In a first step, N-(2-aminophenyl)-4-methyl-thiazolin-2-thione is transformed into a mono- or disubstituted urea at nitrogen, and then in a second step, alkylated at sulfur. The resulting salts, after treatment with a base, gave S-alkylcarbamothioates in high isolated yields together with 3-methyl[1,3]thiazolo[3,2-a]benzimidazole under very mild conditions.
Practical synthesis of S-alkyl thiocarbamate herbicides by carbonylation of amines with carbon monoxide and sulfur
Mizuno, Takumi,Iwai, Toshiyuki,Ito, Takatoshi
, p. 2869 - 2873 (2007/10/03)
An industrial and economic carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamate herbicides. In the presence of potassium carbonate and solvent DMSO, S-alkyl thiocarbamates, such as thiobencarb and orbencarb (herbicides) are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1atm, 20°C).
Novel synthesis of S-alkyl thiocarbamates from amines, carbon monoxide, elemental sulfur, and alkyl halides in the presence of a selenium catalyst
Mizuno, Takumi,Nishiguchi, Ikuzo,Sonoda, Noboru
, p. 5669 - 5680 (2007/10/02)
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
Mizuno, Takumi,Nishiguchi, Ikuzo,Hirashima, Tsuneaki
, p. 2403 - 2412 (2007/10/02)
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.
The Synthesis of Alkyl Thiocarbamates in an Ultrasonic Field
Galiakhmetov, R. N.,Valitov, R. B.,Kurochkin, A. K.,Margulis, M. A.
, p. 614 - 615 (2007/10/02)
The synthesis of alkylthiocarbamates from an alkali metal salt of thiocarbamic acid and halogenohydrocarbons in an aqueous medium has been investigated with exposure to ultrasound and without such exposure but under conditions of vigorous stirring.The intensifying effect of ultrasound on the synthesis thiocarbamates has been demonstrated.
Process for preparing esters of thiolcarbamic acids
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, (2008/06/13)
The invention relates to a new process for preparing known thiolcarbamate esters of the general formula (I) STR1 wherein R1 and R2 stand independently for hydrogen or a straight or branched chain alkyl group containing 1 to 6 carbon atoms or an alkenyl group containing 2 to 6 atoms, or an alkyl group containing 1 to 6 or an alkenyl group containing 2 to 6 carbon atoms and mono- or polysubstituted by halogen, oxygen, sulphur and/or nitrogen; or R1 and R2 together may represent an optionally substituted α,ω-alkylene group containing 4 to 6 carbon atoms; R3 and R4 stand independently for hydrogen or an alkyl group containing 1 to 4 carbon atoms and optionally substituted by halogen or by a group containing oxygen, sulphur and/or nitrogen; and R5 and R6 both stand for hydrogen; or R5 and R6 together may represent a chemical bond. The compounds of general formula (I) are prepared by reacting (a) thiolcarbamate salts of the general formula (II) STR2 wherein the meanings of R1 and R2 are as defined above, and Y stands for a primary, secondary or tertiary ammonium ion or an alkaline metal ion; or (b) amines of the general formula (III) STR3 wherein the meanings of R1 and R2 are as defined above, together with sulphur and carbon monoxide; or (c) amine of the general formula (III) together with carbonyl sulphide with alkynes of the general formula (IV) wherein the meanings of R3 and R4 are as defined above and, if desired, hydrogenating the obtained product of general formula (I), wherein the meanings of R1, R2, R3 and R4 are as defined above and R5 together with R6 forms a chemical bond, to a compound of the general formula (I), wherein both R5 and R6 stand for hydrogen.
