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A new knowledge about the synthesis of 1-phenyl-3-(2-cyanophenyl)thiourea

P. Pazdera, E. Nováček, and D. Ondráček

Department of Organic Chemistry, Faculty of Natural Sciences, J. E. Purkyně University, CS-61137 Brno

 

Abstract: The addition of 2-aminobenzonitrile to phenyl isothiocyanate repro­ ducing the procedure described in literature [1] did not lead to 1-phenyl-3-(2-cyanophenyl)thiourea but to the product of its cyclization, i.e. 3-phenyl-4-imino-l,2,3,4-tetrahydroquinazoline-2-thione. This was the only product of the addition, even under varied conditions. The reaction of 2-aminobenzonitrile with 4-nitrophenyl isothiocyanate under various conditions was studied. The only product formed was 4-imino-3-(4-nitrophenyl)-1,2,3,4-tetrahydroquinazoline-2-thione. l-Phenyl-3-(2-cyanophenyl)thiourea was prepared by the addition of aniline to 2-isothiocyanatobenzonitrile at room temperature in the mixture dichloromethane—petroleum ether. So far unknown 2-isothiocyanatoben­zonitrile was prepared by the reaction of thiophosgene with 2-aminoben­zonitrile in the mixture dichloromethane—water.

Full paper in Portable Document Format: 433a465.pdf

 

Chemical Papers 43 (3) 465–470 (1989)

Monday, November 23, 2020

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