Benzothiazole → HCID 86690039, compound

Participants

Reaction Steps

4-methoxybenzoylchloride (7.0 g, 41.0 mmol) was added dropwise to a stirring solution of benzothiazole (5.4 g, 40.0 mmol) in dichloromethane (40 mL) under argon atmosphere. A catalytic amount of AlCl3 and trimethylsilylcyanide (4.1 g, 42.0 mmol) were than added into the reaction mixture. After being stirred for 14 h at room temperature, the reaction mixture was evaporated to dryness in vacuo and the residue was triturated with ether to give 3-(4-methoxybenzoyl)-2,3-dihydrobenzo[d]thiazole-2-carbonitrile, 8.2 g (70%); mp 122-123° C. (Lit.21 122-123° C.). 1H NMR (DMSO-d6) δ 3.82 (3H, s, MeO), 6.72 (1H, brs, C2-H), 6.84 (1H, s, ArH), 7.01-7.14 (4H, m, 4×ArH), 7.52-7.55 (3H, m, 3×ArH).

Provenance & Evidence