Imidazole → HCID 54166792, compound

Participants

Reaction Steps

A solution of 2-cyano-6-hydroxybenzothiazole (5.0 g, 28 mmol) in 100 ml of anhydrous DMF under inert atmosphere was treated with 2.9 g of imidazole (4.2 mmol) followed by t-butyldiphenylchlorosilane (9.34 g, 34 mmol). The reaction was stirred at room temperature for 3 h and then diluted with 200 ml of ethyl acetate and washed with water (4×400 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography, eluting with 5-10% ethyl acetate/hexanes to afford 13.0 g of the desired product containing ~10% silyl impurity in quantitative yield. The product was taken on without further purification. 1H NMR (CDCl3): δ 1.12 (s, 9H) ; 7.13-7.46 (m, 8H); 7.70-7.72 (m, 4H); 7.92-7.95 (d, 1H).

Provenance & Evidence