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 head 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, solidfied. The solid had a melting point of 61° C.-63° C.

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

ORD record

ord-d2cf2094e96942c79660a51f111ae747

Source dataset

uspto-grants-1982_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04314840