Water → HCID 11666408, compound

Participants

Reaction Steps

To a solution of 2-hydroxy-4,5,6,7-tetrahydrobenzothiazole (335 mg, 2.16 mmol) in DMF (3 mL) was added NaH (101 mg, 2.52 mmol). After stirring 10 minutes at room temperature, a solution of 2-bromo-4′-methylacetophenone (668 mg, 2.82 mmol) in DMF (5 mL) was added and the mixture was stirred overnight. Water was added and the mixture was extracted with EtOAc, dried over MgSO4 and the solvent was evaporated. The oil recovered was purified by flash chromatography on silicagel (CH2Cl2) to give 29 as a solid in 65% yield: mp 108-110° C.; 1H-NMR (DMSO-d6) 1.73 (s, 4H), 2.19 (s, 2H) 2.40 (m, 5H), 5.23 (s, 2H), 7.39 (d, 2H), 7.95 (d, 2H); Anal. (C16H17NO2S) C, H, N.

Provenance & Evidence