Ethylene Glycol → HCID 20551713, compound

N-(2,2-Dimethoxyethyl)-2-chloroacetamide (18.1 grams; 0.10 mole) ethylene glycol (6.82 grams; 0.11 mole) and 10 drops of a solution of one gram of p-toluenesulfonic acid in 100 ml of diethyl ether were charged into a glass reaction vessel fitted with a mechanical stirrer, thermometer, distillation heat and condenser. The mixture was stirred and heated to about 95° C. to 100° C. Byproduct methanol was distilled off. When no further methanol was evolved, the mixture was cooled to room temperature, sodium carbonate (2 grams) was added and the slurry was stirred for a period of about 1 hour. The slurry was then filtered and the filtrate fractionally distilled under reduced pressure the desired product N-(1,3-dioxolan-2-ylmethyl)-2-chloroacetamide was obtained as a fraction boiling at 109° C.-110° C. at 0.15 mm Hg which, when cooled, solidified. The solid had a melting point of 61° C.-63° C.

1. customfitted with a mechanical stirrer
2. distillationthermometer, distillation
3. temperatureheat
4. temperatureheated to about 95° C. to 100° C
5. distillationByproduct methanol was distilled off
6. additionsodium carbonate (2 grams) was added
7. stirringthe slurry was stirred for a period of about 1 hour
8. filtrationThe slurry was then filtered
9. distillationthe filtrate fractionally distilled under reduced pressure the desired product N-(1,3-dioxolan-2-ylmethyl)-2-chloroacetamide
10. customwas obtained as a fraction boiling at 109° C.-110° C. at 0.15 mm Hg which, when
11. temperaturecooled

ORD record

ord-bb6d67765e2c47b09b6ac6dd1eb22a2c

Source dataset

uspto-grants-1980_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04237056