Ethylene Glycol → N-methyl-N-(1,3-dioxolan-2-ylmethyl)-alpha-chloroacetamide

HRID 1446955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446955
[CH3:1][N:2]([CH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10])[C:3](=[O:6])[CH2:4][Cl:5].C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[O:9]1[CH2:10][CH2:12][O:11][CH:8]1[CH2:7][N:2]([CH3:1])[C:3](=[O:6])[CH2:4][Cl:5]

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 128507002-Chloro-N-(2,2-dimethoxyethyl)-N-methylacetamide

Produkt 1

HCID 12850701N-methyl-N-(1,3-dioxolan-2-ylmethyl)-alpha-chloroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

N-Methyl-N-(2,2-dimethoxyethyl)-2-chloroacetamide (19.5 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 100° C. to 110° 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)-N-methyl-2-chloroacetamide was obtained as a fraction boiling at 124° C. at 0.30 mm Hg and at 119° C. at 0.15 mm Hg.

Aufarbeitung

  1. customfitted with a mechanical stirrer
  2. distillationthermometer, distillation head and condenser
  3. temperatureheated to about 100° C. to 110° 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

Quellen und Nachweise

ORD-Eintrag
ord-cd003996d60b47a686229db101df259f
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04314840

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