4-Toluenesulfonyl chloride → HCID 59276512, compound

Participants

Reaction Steps

2-(Methoxymethyl)-5-nitro-1-tosyl-1H-benzo[d]imidazole. 2-(Methoxymethyl)-5-nitro-1H-benzo[d]imidazole (1.23 g, 5.94 mmol) and 4-methylbenzene-1-sulfonyl chloride (1.358 g, 7.12 mmol) were dissolved in tetrahydrofuran (50 mL) and sodium tert-butoxide (1.141 g, 11.87 mmol) was added. The mixture was stirred at room temperature for 16 h. The reaction mixture was poured into a separatory funnel containing water and 50% ethyl acetate. The organic layer was concentrated on a rotary evaporator nearly to dryness and purified on silica column eluting with 0-50% ethyl acetate in hexane. The fractions containing product were concentrated on a rotary evaporator to give the desired product as white solid (0.9 g, 42% yield). MS (ESI) m/z 362.3 [M+1]+.

Provenance & Evidence