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

Temperature

0 °C

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.

1. waitfor 14 hours at room temperature
2. filtrationfiltered
3. customevaporated to dryness at 40° C.
4. dissolutionthe residue was dissolved in chloroform
5. additionThe resulting solution was mixed with 1N hydrochloric acid
6. additionby mixing with 10% aqueous sodium carbonate and aqueous saturated sodium chloride
7. dry with materialIt was then dried over anhydrous magnesium sulphate
8. filtrationfiltered through activated charcoal
9. customevaporated to dryness

ORD record

ord-b006a892e99a47c38ab3f1e93c26cac2

Source dataset

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04795627