Acetamide, N-(2-methoxyphenyl)- → Acetamide, N-(5-((butylamino)sulfonyl)-2-methoxyphenyl)-

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Reaction Steps

As shown in Eq. 1 (above), o-acetanisidide (100 gms., 0.605 mole) was added in portions to 200 ml of chlorosulfonic acid at about 50° C. (cooling was necessary). After the addition, the amber solution was heated at about 50° to 60° C. for four hours, cooled to room temperature and carefully added to an ice water mixture (1.5 kg). A white precipitate was collected, washed free of acid, and pressed dry. A portion of sulfonyl chloride (0.100 mole) was dissolved in 100 ml of tetrahydrofuran and treated with 16.1 gms (0.221 mole) of n-butylamine (exotherm to 50° C.). The reaction mixture was refluxed an additional 15 minutes, the condenser removed, and the solvent removed by heating. The white crystalline solid that remained was slurried with 100 ml of water, collected and dried to give 27.7 gms (92.4 percent) of the sulfonamide (melting point 115°-117° C).

Provenance & Evidence