Chloroacetyl chloride → HCID 899189, compound

Participants

Reaction Steps

A solution of 3-nitroaniline (1.00 g, 7.24 mmol) in THF (20 ml) was cooled to 4° C. in an ice bath. To this stirred mixture TEA (1.47 g, 14.50 mmol), then chloroacetyl chloride (0.98 g, 8.70 mmol) were sequentially added. The reaction was allowed to warm up to room temperature and after 2 and a half hours diethylamine (1.59 g, 21.7 mmol) was added in ice bath and the resulting mixture stirred overnight at room temperature. After completion (TLC 5% MeOH in DCM), solvent was evaporated in vacuo. The crude product was dissolved in DCM (75 ml), washed 3 times with saturated aqueous NaHCO3 solution (50 ml), dried (MgSO4), filtered and taken to dryness in vacuo. The crude product thus obtained was purified by flash column chromatography (0%-5% MeOH in DCM) to give 2-(diethylamino)-N-(3-nitrophenyl)acetamide 4 as a yellow semi-solid (0.92 g, 50%); Rf 0.26 [5% MeOH in DCM]; δH (CDCl3, 400 MHz) 9.68 (1H, s, NH), 8.36-8.35 (1H, m, ArH), 8.05-8.03 (1H, m, ArH), 7.93 (1H, dd, J1=8.4 Hz, J2=1.6 Hz, ArH), 7.51.7.57 (1H, m, ArH), 3.18 (2H, s, CH2), 2.67 (4H, quartet, J=7.2 Hz, 2×CH2), 1.10 (6H, t, J=7.2 Hz, 2×CH3); δC (CDCl3, 100 MHz) 169.95 (C═O), 147.27 (Ar—C), 138.64 (Ar—C), 129.61 (Ar—CH), 110.74 (Ar—CH), 109.17 (Ar—CH), 105.92 (Ar—CH), 58.14 (CH2), 48.79 (2×CH2), 12.39 (2×CH3); LC-MS (5 min) m/z 252.37 [C12H17N3O3+H]+ (100), Rt 0.83 min; HRMS m/z calc C12H18N3O3 [M+H]+252.1353. found [M+H]+252.1358; anal. CHN calc. C12H17N3O3. C, 57.4%; H, 6.8%; N, 16.7%. found C, 57.3%; H, 7.1%; N, 16.6%.

Provenance & Evidence