Ammonium Chloride → HCID 89545277, compound

Participants

Reaction Steps

To a solution of N-methyl-1,2,4-thiadiazol-5-amine (0.64 g, 5.5 mmol) in tetrahydrofuran (15 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1 M solution in tetrahydrofuran, 6.1 mL, 6.1 mmol). The reaction mixture was allowed to warm to ambient temperature and was stirred for 1 hr. The mixture was cooled to −78° C., and a solution of 2,4,5-trifluorobenzenesulfonyl chloride (0.85 mL, 6.1 mmol) in tetrahydrofuran (5 mL) was added. The reaction mixture was allowed to warm to ambient temperature, stirred for 1 h and saturated aqueous ammonium chloride (10 mL) was added. The mixture was extracted with ethyl acetate (4×20 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 10-30% gradient of ethyl acetate in hexanes to afford 2,4,5-trifluoro-N-methyl-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a colorless solid in 50% yield (0.864 g): 1H NMR (300 MHz, CDCl3) δ8.28-8.18 (m, 1H), 7.97-7.84 (m, 1H), 7.20-7.07 (m, 1H), 3.61 (s, 3H); MS (ES+) m/z 309.7 (M+1).

Provenance & Evidence