Hydroxylamine → 2-{[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxy-benzyl)amino}-N-hydroxy-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 48.81 g (0.114 mol) of {[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxybenzyl)-amino}-acetic acid in 500 ml of CH2Cl2, 19.56 ml (0.228 mol) of oxalyl chloride and 0.88 ml (0.011 mol) of DMF are added dropwise at 0-5° C. under N2 atmosphere. The mixture is stirred for 1 h at 0-5° C. and 1 h at r.t. To a solution of 226 ml (3.42 mol) of) 50% hydroxylamine in H2O (Aldrich) in 1200 ml of THF, a solution of the freshly prepared above acid chloride in CH2Cl2 is added over 45 min. at −10 to −5° C. through a teflon tube using N2 gas pressure. The reaction mixture is stirred for 30 min at −5 to 0° C. and filtered through, paper filter to remove insoluble precipitates. The filtrate is diluted with H2O and extracted with CH2Cl2. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The product is collected by filtration and washed with ether to give 43.03 g of 2-{[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxy-benzyl)amino}-N-hydroxy-acetamide; NMR (CDCl3): 2.2-2.35 (m, 2H), 3.69 (s, 2H), 3.76 (t, 2H, J=6 Hz), 3.79 (s, 3H), 4.21 (t, 2H, J=6 Hz), 4.26 (s, 2H), 6.77 (br s, 1H), 6.85 (d, 2H, J=9.04 Hz), 7.03 (d, 2H, J=9.04 Hz), 7.15 (d, 2H, J=9.04 Hz), 7.78 (d, 2H, J=8.56 Hz), 8.82 (br s, 1H).

Provenance & Evidence