2-chloro-N,N-dimethylacetamide → 2-hydroxyethoxy-acetic acid N,N-dimethylamide

HRID 1513551Notes

Reaction equation

HRID 1513551 reaction equation
[Na].[CH2:2]([OH:5])[CH2:3][OH:4].[CH3:6][N:7]([CH3:12])[C:8](=[O:11])[CH2:9]Cl>C(O)CO>[CH3:6][N:7]([CH3:12])[C:8](=[O:11])[CH2:9][O:4][CH2:3][CH2:2][OH:5]

Participants

4

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 86592871Ethylene glycol monosodium salt

Product 1

HCID 167525962-hydroxyethoxy-acetic acid N,N-dimethylamide

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
50 °C

Procedure

40 ml of ethylene glycol and 8.4 g (0.1 mole) ethylene glycol monosodium salt are weighed into a 100 ml round bottom flask. The reaction mixture is heated to 50° C. with stirring and at this temperature, 12.2 g (0.1 mole) of chloroacetic acid N,N-dimethylamide are added dropwise in 1 hour. The reaction mixture is kept at the same temperature for further 1 hour and subsequently submitted to fractionated distillation. The first fraction (boiling temperature approx. 80° C., 260 Pa) comprises the solvent ethylene glycol. The boiling temperature of the product fraction is 130-135° C. (13 Pa). The purity of the product is higher than 98% as determined by gas chromatography.

Workup

  1. additionare added dropwise in 1 hour
  2. distillationdistillation
  3. customis 130-135° C.

Sources & evidence

ORD record
ord-2f5119ab0da64d40824d235ba2929979
Source dataset
uspto-grants-2012_07
Patent number
US08217200B2

Reaction notes

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