Sodium Carbonate → N-(1-Chlorobutan-2-yl)acetamide

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Reaction Steps

A sample of N-[1-(chloromethyl)propyl]acetimidoyl chloride from Example 8 is treated with an excess of 10% aqueous sodium carbonate solution at room temperature. The organic material is extracted with ether and dried over MgSO4. Removal of the solvent under reduced pressure leaves N-[1-(chloromethyl)propyl]acetamide as a crystalline solid in nearly quantitative yield. An infrared spectrum shows peaks at 3300(M), 3100(W), 1650(S), and 550(S) cm-1 ; nuclear magnetic resonance (CDCl3) shows peaks 0.95 ppm (t ,3H), 1.4-1.8 ppm (m ,2H), 2.03 ppm (s ,3H), 3.67 ppm (d,2H,CH2Cl), 3.8-4.4 ppm (m ,1H).

Provenance & Evidence