Hydrochloric Acid → 3-[(3-Carboxypropyl)amino]-4-phenoxy-5-sulfamoylbenzoic acid

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Reaction Steps

The chlorobutyramide 3-(γ-chlorobutyrylamino)-4-phenoxy-5-sulfamylbenzoic acid (11.0 g) was added to a solution of KOH (40 g) in water 100 ml. The resulting solution was stirred and heated under reflux overnight. After cooling it was acidified with 3N acqueous HCl, chilled by adding ice and the product collected, washed and air-dried. A recrystallization from aq. acetone gave 9.80 g (77% on two steps) of N-(2-phenoxy-3-sulfamyl-5-carboxyphenyl)-γ-aminobutyric acid as colorless crystals with m.p. 240°-241°; ir (Nujol) 3400, 3300, 2600 (broad), 1700, 1610, 1590, and 1550 cm-1 ; nmr (CDCl3 /d6 -DMSO) 1.4-2.3 (m, 4H), 3.15 (m, 2H), 4.2 (broad, NH), 6.43 (s, SO2NH2), 6.65-7.4 (m, C6H5), 7.57 (d, J=2, CH), and 7.92 ppm (d, CH); mass spectrum m/e 283 (100%) and 394 (M+ ).

Provenance & Evidence