Ethylene Glycol → HCID 20307404, compound

HRID 1763785Notes

Reaction equation

HRID 1763785 reaction equation
[CH3:1][CH:2]([N:8]([CH2:13][CH:14]([O:18][CH2:19][CH3:20])[O:15]CC)[C:9](=[O:12])[CH2:10][Cl:11])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].C(O)CO.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:1][CH:2]([N:8]([CH2:13][CH:14]1[O:15][CH2:20][CH2:19][O:18]1)[C:9](=[O:12])[CH2:10][Cl:11])[CH2:3][CH2:4][CH:5]([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 69252-Methylbenzenesulfonic acidHCID 10340Sodium CarbonateHCID 20307414HCID 20307414, compound

Product 1

HCID 20307404HCID 20307404, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(1,4-Dimethylpentyl)-N-(2,2-diethoxyethyl)-α-chloroacetamide (10 grams), ethylene glycol (2 grams) and trace amounts of toluenesulfonic acid were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux until no more ethanol was given off. After this time sodium carbonate (1 gram) was added to the mixture with stirring and the resulting mixture was distilled to yield the desired product N-(1,4-dimethylpentyl)-N-(1,3-dioxolan-2-ylmethyl)-α-chloroacetamide having a boiling point of 200° to 205° C. at 1 mm of Hg pressure.

Workup

  1. additionwere charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. temperaturethermometer and reflux condenser
  4. temperatureThe reaction mixture was heated
  5. distillationthe resulting mixture was distilled

Sources & evidence

ORD record
ord-a5409ab8447247209958f2ef06602d03
Source dataset
uspto-grants-1978_09
Patent number
US04113464

Reaction notes

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