Hydrochloric Acid → HCID 23760999, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(methylsulfonyl) benzoic acid (3.1 g, 15.5 mmol) in 100 mL of methylene chloride was added dimethylformamide (1.2 mL, 15.5 mmol). The reaction vessel was cooled to 0° C. and oxalyl chloride (3.1 mL, 35 mmol) was added. The mixture stirred 1 h at 0° C. and was added to a solution of N-(1-(5-methyl-fur-2-yl)ethyl) hydroxylamine (2.6 g, 18.6 mmol) and triethylamine (3.3 mL, 23.3 mmol) in 75 mL methylene chloride at 0° C. The mixture stirred 1.5 h and was poured into 2M HCl (100 mL). The aqueous layer was extracted with methylene chloride (3×, 100 mL) and the combined organic extract was washed with saturated sodium bicarbonate solution (1×100 mL) and brine (1×100 mL). The solution was dried over MgSO4, filtered and evaporated. The material was recrystallized from ethyl acetate to yield 1.14 g of a white solid; m.p.=177° C.; 1H NMR (300 MHz, DMSO-d6) 9.85 (bs, 1H), 7.97 (d, J=8.41 Hz, 2H), 7.83 (d, J=9.01 Hz, 2H), 6.24 (d, J=3.60 Hz, 1H), 6.02 (m, 1H), 5.71 (bs, 1H), 3.26 (s, 3H), 2.24 (s, 3H), 1.47 (d, J=6.91 Hz, 3H). MS (M+H)+ =324; Analysis calc'd for C15H17NO5 : C, 55.20; H, 5.25; N, 4.29. Found: C, 55.07; H, 5.20; N, 4.23.

Provenance & Evidence