Stannous Chloride → 4-(3-Methyl-1,2,4-thiadiazol-5-yl)aniline

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-methyl-5-(4-nitro-phenyl)-[1,2,4]thiadiazole (104 mg, 0.423 mmol, CAS 800408-77-9) in ethanol (4.3 mL) was added tin(II) chloride (401 mg, 2.1 mmol) and the reaction was heated to 70° C. for 4 hours. The yellow solution was poured onto saturated aqueous sodium hydrogen carbonate solution and the mixture was stirred for 30 minutes. The precipitate was filtered off, washed with water. The solid was heated 3 times with tetrahydrofurane and filtered. The collected organic layers were evaporated to yield crude title compound (110 mg, quant.) as a yellow solid. MS ISP (m/e): 192.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=7.64 (d, 2H), 6.63 (d, 2H), 6.01 (br s, 2H), 2.54 (s, 3H).

Provenance & Evidence