Trichloromethanethiol → 5-Chloro-3-p-tolyl-[1,2,4]thiadiazole

Participants

Reaction Conditions

Reaction Steps

To a mixture of p-methylbenzamidine hydrochloride (5.1 g, 30.0 mmol) in CHCl3 (100 ml) is added triethyl amine (15.12 g, 20.9 ml, 150.0 mmol) and cooled to 5° C. in an ice-water bath. To the mixture is slowly added perchloromethyl mercaptan (95%, 6.16 g, 31.5 mmol) in CHCl3(10 ml) over 1 hour. The yellow solution is allowed to warm up to room temperature. After 2 hours the mixture is washed with water (100 ml×2) and brine (100 ml). The organic layer is dried over MgSO4 and the solvent is removed under reduced pressure to yield a brown oil. The oil is purified on a bed of silica gel, eluting with 1:1 CHCl3:hexanes to yield 3-(p-tolyl)-5-chloro-1,2,4-thiadiazole as a yellow solid (2.78 g, 44%). 1H NMR (CDCl3): δ 2.41 (s, 3H), 7.30(d, 2H), 8.13 (d, 2H).

Provenance & Evidence