Dichloromethane → HCID 21507562, compound

Participants

Reaction Steps

2.4 g of N-(2-aminoindane-5-sulfonyl)-N'-cyclopentyl-methylurea (melting point 192° - 194° C, prepared by saponification of 2-N-(acetamido-indane-5-sulfonyl)-N'-cyclopentyl-methyl-urea, melting point 107° - 109° C) were dissolved in 10 ml of water and 3.6 ml of 2N-sodium hydroxide solution. Then, a solution of 1.7 g of 5-chloro-2-methoxy-benzoyl chloride in 6 ml of methylene chloride was added dropwise, while cooling, and the whole was stirred for 1 hour; the mixture was slowly heated and the methylene chloride was evaporated. The sulfonyl-urea that had precipitated was filtered off with suction and dissolved in dilute sodium hydroxide solution. The whole was then treated with active charcoal, filtered and the sodium salt was precipitated by the addition of concentrated sodium hydroxide solution. The sodium salt was dissolved in water and precipitated again by the addition of sodium hydroxide solution. Finally, the free compound was precipitated from the alkaline solution with hydrochloric acid and recrystallized from methanol. Melting point 194° - 196° C.

Provenance & Evidence