Chloroacetyl chloride → 2-Chloro-N-ethyl-N-(2-hydroxyethyl)acetamide

Participants

Reaction Conditions

Reaction Steps

Chloroacetylchloride (97 g., 1 mole) in dry acetonitrile (100 ml) was added dropwise to a cold (0° C.) solution of N-ethylethanolamine (89 g., 1 mole) in acetonitrile (150 ml) and anhydrous sodium carbonate (119 g., 1.1 mole). The mixture was mechanically stirred for two hours at 0° C. and then for 14 hours at room temperature, filtered, evaporated to dryness at 40° C. and the residue was dissolved in chloroform. The resulting solution was mixed with 1N hydrochloric acid, followed by mixing with 10% aqueous sodium carbonate and aqueous saturated sodium chloride. It was then dried over anhydrous magnesium sulphate, filtered through activated charcoal and evaporated to dryness to yield N-chloroacetyl-N-ethyl-ethanolamine as a colorless oil (yield 85%) with the following indicia: MS m/e 165 (M+); 88 (M--COCH2Cl); since the IR spectrum of the liquid showed two C=O peaks, one minor at λmax 1750 cm-1 (C=O, ester) and one major at 1635 cm-1 (C=O, amide), the compound was purified on an alumina dry column using chloroform and chloroform:methanol (9:1) as eluents. The purified amide showed only one C=O group at 1635 cm-1. This pure compound (pure by TLC (thin layer chromatography), NMR (nuclear magnetic resonance), IR (infrared), MS (mass spectometry) was used for the next step. The NMR (250 MHz) of the pure amide showed peaks of the two structures which are at equilibrium in such amides: ##STR13## Therefore, δCDCl3ppm : 4.3 ##STR14## 3.9-3.2 (m, --CH2 --N--CH2CH2O--); 1.18 (--CH3, q, e.g., overlap of two triplets) s: singlet; m: multiplet; q: quartet.

Provenance & Evidence