14467-74-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 3425, 1953 DOI: 10.1021/ja01110a037

Upstream product

• 13464-19-2 phenyl chlorothioformate 
• 75-04-7 ethylamine 
• 108-98-5 thiophenol 
• 109-90-0 ethyl isocyanate 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 627-45-2 N-formylethylamine 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 623-76-7 N,N'-diethylurea 
• 65608-76-6 1-(4-Chloro-benzyl)-3-ethyl-urea 
• 71475-35-9 lozilurea 
• 65608-86-8 1-Ethyl-3-(4-methyl-benzyl)-urea 
• 39054-20-1 Chloromethyl-ethyl-thiocarbamic acid S-phenyl ester 

Relevant academic research and scientific papers

Synthesis of thiocarbamates from thiols and isocyanates under catalyst- and solvent-free conditions

A simple and efficient procedure was developed for the synthesis of S-alkyl (aryl) thiocarbamates under solvent-free conditions without the use of a catalyst. The significant features of this protocol are (a) operational simplicity, (b) mild reaction cond

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.

Kinetics and mechanism of the aminolysis of aryl N-ethyl thiocarbamates in acetonitrile

The aminolysis of aryl N-ethyl thiocarbamates (EtNHC(=O)SC 6H4Z) with benzylamines (XC6H 4-CN2NH2) in acetonitrile at 30.0 °C is investigated. The rates are faster than the corresponding values for aryl N-phenyl thiocarbamates (PhNHC(=O)SC6H4Z), reflecting a stronger push to expel the leaving group by EtNH than the PhNH nonleaving group in a concerted process. The negative ρXZ (-0.86) and failure of the reactivity-selectivity principle found are consistent with the concerted mechanism. The kinetic isotope effects involving deuterated nucleophiles (k H/kD = 1-5-1.7) and low ΔH? with large negative ΔS? values suggest a hydrogen bond cyclic transition state.