Hydroxyamine hydrochloride → 6-(Anilinosulfonyl)-N-hydroxyhexanamide

Participants

Reaction Steps

To a mixture of ethyl 6-(anilinosulfonyl)hexanoate (64b) and hydroxylamine hydrochloride (0.43 g, 6.2 mmol) in methanol (5 ml) the 3.43 N solution of sodium methylate (2.62 ml, 9.0 mmol) in methanol was added and the reaction was stirred at ambient temperature for 40 min. The reaction mixture was poured into saturated NaH2PO4 (15 ml) and extracted with ethyl acetate. The extract was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was evaporated, the residue was washed with diethyl ether and crystallised from ethyl acetate. The title compound (0.3 g, 69%) was obtained as white crystals, m.p. 97–98° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.02–1.78 (m, 6H, CH2); 1.90 (br t, 2H, J=6.4 Hz, CH2); 3.06 (t, 2H, J=7.0 Hz, CH2); 6.94–7.60 (m, 5H, arom.); 8.66 (br s, 1H, NH); 9.76 (br s, 1H, NH); 10.36 (br s, 1H, OH). HPLC analysis on Symmetry C8 column: impurities 3.5% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer (pH 2.5), 30:70; detector UV 220 nm; flow rate 1.1 ml/min; sample concentration 0.4 mg/ml). Anal. Calcd for C12H18N2O4S, %: C, 50.33; H, 6.34; N, 9.78; S, 11.20. Found, %: C, 50.10; H, 6.22; N, 9.83; S, 11.10.

Provenance & Evidence