Ethyl Acetate → 3,4-diamino-N-(cyclopentyloxy)benzenesulfonamide

반응식

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:18]([O-])=O.C(OCC)(=O)C>[Pd].C(O)C>[NH2:18][C:3]1[CH:4]=[C:5]([S:8]([NH:11][O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:9])=[O:10])[CH:6]=[CH:7][C:2]=1[NH2:1]

참가 물질

실험 절차

A solution of 4-amino-N-(cyclopentyloxy)-3-nitrobenzenesulfonamide (4.50 g, 14.95 mmol) in 1:1 ethyl acetate:ethanol (150 mL) was combined with 5% Pd on barium sulfate and reduced under a hydrogen atmosphere over 72 hours. The reaction mixture was filtered through a pad of diatomaceous earth and evaporated in vacuo to a residue which crystallized on standing. The solid was slurried in hexane, filtered and dried under high vacuum to provide 3,4-diamino-N-(cyclopentyloxy)benzenesulfonamide (4.086 g, 100%) as a light brown solid H1-NMR (dimethylsulfoxide-D6): 1.61 (m, 8H), 4.37 (m, 1H), 4.90 (b, 2H), 5.38 (b, 2H), 6.57 (d, 1H), 6.88 (m, 1H), 6.96 (d, 1H), 9.64 (s, 1H). MS(ESI): 272(M+H).