Ethyl Acetate → 5-Methyl-5H-pyrazolo[3,4-d]-1,2,3-thiadiazole-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

The compound, 5-methylpyrazolo-1,2,3-thiadiazole-6-carboxamide (0.9 g, 4.92 mmol) was slurried in toluene (10 mL) and thionyl chloride (0.5 mL) was added. The mixture was heated to 80° C. and then to 105° C. with no reaction. The mixture was cooled to 70° C. and ethyl acetate (10 mL) was added. The slurry was stirred at 70° to 80° C. for 55 h, cooled and concentrated onto Silica Woelm®TSC and chromatographed on 50 g of the same silica (25% ether-hexane) to give after a 300 mL forerun 0.2 g of 6-cyano-5-methylpyrazolo-1,2,3-thiadiazole as a light yellow solid; mp 111° to 114° C.; 1H-NMR (CDCl3) σ 4.41 (s, 3H); IR (KBr) 2230, 1332, 679 cm-1 ; Mass spec. m/e 165.0109; m/e calcd. for C5H3N5S 165.0109.

Provenance & Evidence