Benzenesulfonamide → 5-(benzenesulfonyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole

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Reaction Steps

Benzenesulfonamide (638 mg) and 4,5-bis(bromomethyl)thiazole (M. Al. Hariri, O. Galley, F. Pautet, H. Fillion, Eur. J. Org. Chem., pp. 593-594 (1998)) (1.10 g) were dissolved in N,N-dimethylformamide (10 mL) under ice cooling, and sodium hydride (60% in oil, 357 mg) was added thereto at a time, followed by stirring at room temperature for 3 hours. The resultant mixture was partitioned between water and methylene chloride, and the organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away, and the residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=9:1), to thereby give the title compound (137 mg).

Provenance & Evidence