Unsaturated compounds containing nitrogen. Part II. The preparation and thermal rearrangement of 1,4-diphenyl-1-thiocyanato-2,3-diazabuta-1,3-diene (α-thiocyanatobenzylidenehydrazonotoluene) and related reactions

Abstract

1-Chloro-1,4-diphenyl-2,3-diazabuta-1,3-diene reacts with potassium thiocyanate to give 1,4-diphenyl-1-thiocyanato-2,3-diazabuta-1,3-diene in high yield. Thermal rearrangement of the thiocyanate at ca. 130° gives 2-benzylideneamino-5-phenyl-1,3,4-thiadiazole and higher molecular-weight material. Acid hydrolysis of the thiocyanate affords benzaldehyde and 2-amino-5-phenyl-1,3,4-thiadiazole.