64651-83-8

Upstream product

• 13606-10-5 chloro-thioformic acid (4-chloro-phenyl)ester 
• 62-53-3 aniline 
• 106-54-7 p-Chlorothiophenol 
• 3422-01-3 tert-butyl phenylcarbamate 
• 201230-82-2 carbon monoxide 
• 98-95-3 nitrobenzene 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 1467-21-6 N-phenyl-N'-benzylurea 
• 106-54-7 p-Chlorothiophenol 
• 1967-26-6 N-(4-chlorophenyl)-N'-phenylurea 
• 3746-53-0 N-(4-metoxyphenyl)-N'-phenylurea 
• 62-53-3 aniline 
• 35337-68-9 4-Chloro-benzenethiol anion 
• 103-71-9 phenyl isocyanate 

Relevant academic research and scientific papers

One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines

A highly efficient one-pot procedure for the synthesis of carbamates and thiocarbamates has been described. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, the isocyanate intermediates were generated in situ for further reactions with alcohols and thiols to afford the desired carbamates and thiocarbamates in high yields.

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

Kinetics and mechanism of the anilinolysis of S-aryl N-arylthiocarbamates in acetonitrile

The aminolysis reactions of S-aryl N-arylthiocarbamates (YC 6H4NH-C(=O)-SC6H4Z, 1) with anilines in acetonitrile are studied. The reaction rates are more influenced by the nucleophilicity of the nucleophile than the nucleofugality of the leaving group, but the change In the effective charge from reactants to the TS for formation of the tetrahedral intermediate is slightly greater in the leaving group (βz from-0.07 to -0.14) than In the nucleophile (βx = 0.04-0.12). The magnitude of the Broensted coefficients are in the range of values that are consistent for a stepwise mechanism with rate-limiting formation of the zwitterionic tetrahedral intermediate. Signs of cross-interaction constants, ρxy (>0), ρxz (>0) and ρyz (0), are all consistent with a stepwise mechanism. It Is concluded that the change of the amine from benzylamines to anilines causes a shift of the aminolysis mechanism from a concerted to a stepwise process. Copyright

A selenium-catalysed synthesis of thiocarbamates from nitroarenes, carbon monoxide and thiols under mild conditions

An improved method for the selenium-catalysed synthesis of thiocarbamates under mild conditions has been developed. With acetone as solvent, the one-pot selenium-catalysed carbonylation of nitroarenes and thiols with carbon monoxide proceeds smoothly at atmospheric pressure and ambient temperature.

One-pot direct synthesis of thiocarbamates from aniline, carbon monoxide, and thiols catalyzed by selenium

Catalyzed by selenium, oxidative carbonylation of aniline and thiols with carbon monoxide and oxygen affords the corresponding thiocarbamates mostly in moderate to good yields under solvent-free conditions at ambient temperature. Copyright Taylor & Franci

A novel one-pot solvent-free, triethylamine-assisted, selenium-catalyzed synthesis of thiocarbamates from nitroarenes, carbon monoxide, and thiols

A novel one-pot solvent-free synthesis of a series of thiocarbamates is reported. Nitroarenes, carbon monoxide, and thiols are the starting materials, with cheap element selenium as catalyst; this method offers a simple access to thiocarbamates mostly in moderate to good yields. The selenium catalyst can be easily recovered and recycled. Georg Thieme Verlag Stuttgart.

A new one-pot synthesis of thiocarbamates from isocyanates and disulfides in the presence of Zn/AlCl3 system

A novel method has been developed for the synthesis of S-alkyl(aryl) thiocarbamates. The route involves, first, the formation of zinc thiolates by reductive cleavage of disulfides in the presence of Zn/AlCl3 system; then subsequent reaction of

A new and facile route for the synthesis of thiocarbamates from aniline, carbon monoxide, and thiols mediated by selenium

A new and facile route for the synthesis of thiocarbamates was reported. Mediated by selenium, aniline reacts very readily with carbon monoxide and thiols in the presence of triethylamine, to afford the corresponding thiocarbamates mostly in moderate to excellent yields under mild reaction conditions. Selenium can be easily recovered and recycled. Copyright

Nucleophilic Substitution Reactions of Aryl N-Phenyl Thiocarbamates with Benzylamines in Acetonitrile

The aminolysis reactions of aryl N-phenythiocarbamates (PhNHC(=O)SC 6H4Z; 3b) with benzylamines (XC6H 4CH2NH2) acetonitrile are studied. Rates are much faster than the corresponding reactions of aryl N-phenylcarbamates (PhNHC(=O)OC6H4Z; 3a). The rate increase from 3a to 3b is greater than that expected from substitution of thiophenoxide for phenoxide leaving group in the stepwise aminolysis reactions of esters. This large rate increase and the similar change in the aminolysis rates that are reported to occur from aryl ethyl carbonate (EtOC(=O)OC6H4Z; 2a) to aryl ethylthiocarbonate (EtOC(=O)SC6H4Z; 2b) lead us to conclude that the aminolysis of 3b proceeds by a concerted mechanism in contrast to a stepwise process for 3a. The negative ρxz values (-0.63) and violation of the reactivity-selectivity principle (RSP) support the proposed mechanism. The large βx values (1.3-1.5) obtained are considered to indicate a large degree of bond making in the transition state, which is consistent with the relatively large kinetic isotope effects (k H/kD > 1.0) observed.