Diethyl Ether → 2-Chloro-N-(2,2-dimethoxyethyl)-N-methylacetamide

Temperature

-20 °C

The dimethylacetal of 2-methylaminoacetaldehyde (50 grams; 0.42 mole), methylene chloride (200 ml) and triethylamine (46.6 grams; 0.462 mole) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer, addition funnel and calcium chloride drying tube. The reaction mixture was cooled to about -20° C. and chloroacetyl chloride (49.7 grams; 0.44 mole) dissolved in methylene chloride (29 ml) was added dropwise with stirring. After the addition was completed stirring was continued for a period of about 60 minutes at a temperature of from -20° C. to -10° C. The reaction mixture was then stirred at room temperature overnight. After this time ether (125 ml) was added and the reaction mixture was filtered. The filtrate was then washed with water and dilute aqueous sodium hydroxide. The washed solution was dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-methyl-N-(2,2-dimethoxyethyl)-α-chloroacetamide having a boiling point of 117° to 119° C. at 0.30 mm of Hg pressure.

1. customequipped with a mechanical stirrer
2. additionthermometer, addition funnel and calcium chloride drying tube
3. additionwas added dropwise
4. additionAfter the addition
5. stirringwas completed stirring
6. stirringThe reaction mixture was then stirred at room temperature overnight
7. filtrationthe reaction mixture was filtered
8. washThe filtrate was then washed with water and dilute aqueous sodium hydroxide
9. dry with materialThe washed solution was dried over anhydrous magnesium sulfate
10. filtrationfiltered

ORD record

ord-aa57b0fed9a2463a99562e27e054faee

Source dataset

uspto-grants-1978_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04113464