反应详情

A solution of (3,4-dichlorobenzyl)-methylamine (0.50 g, 2.63 mmol) (Shapiro et al. J. Amer. Chem. Soc., (1959) 81, 3725) in a mixture of tetrahydrofuran (20 ml) and 40% aqueous sodium acetate (10 ml) was cooled to 0–5° C. (ice bath) and treated with a solution of acetyl chloride (0.3 g in tetrahydrofuran) added dropwise over 5 min. After 1 h at 0–5° C., the reaction mixture was diluted with ethyl acetate, washed successively with 1 N hydrochloric acid, saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent and distillation of the residue in vacuo gave 0.51 g (83% yield) of the title amide as a clear oil: bp 110–120° C./0.2 torr, (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ (ppm), mixture of rotamers: 2.36 and 2.39 (3H, 2 s, COCH3), 3.16 (3H, s, NCH3), 4.70 and 4.75 (2H, 2 s, NCH2), 7.2–7.7 (3H, m, aromatics). Anal. calcd for C10H11Cl2NO: C, 51.74; H, 4.78; N, 6.03. Found: C, 51.70; H, 4.77; N, 6.04.

1. temperaturewas cooled to 0–5° C. (ice bath)
2. additionadded dropwise over 5 min
3. washwashed successively with 1 N hydrochloric acid, saturated sodium bicarbonate, brine
4. dry with materialdried (magnesium sulfate)
5. customEvaporation of the solvent and distillation of the residue in vacuo