Thionyl Chloride → 2-chloroethoxy-acetic acid-N,N-dimethylamide

HRID 1513555Notes

Reaction equation

HRID 1513555 reaction equation
[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[CH2:4][O:5][CH2:6][CH2:7]O.S(Cl)([Cl:13])=O>ClCCl>[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[CH2:4][O:5][CH2:6][CH2:7][Cl:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 167525962-hydroxyethoxy-acetic acid N,N-dimethylamide

Product 1

HCID 167525952-chloroethoxy-acetic acid-N,N-dimethylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 ml of dichloromethane are transferred into a round bottom flask of 250 ml volume and 30.0 g (0.2 mol) 2-hydroxyethoxy-acetic acid-N,N-dimethylamide are added. The vessel is cooled on ice and 25.0 g (0.21 mole) of thionyl chloride are added to it dropwise in 10 minutes. The reaction mixture is stirred at room temperature for 20 minutes, and the solvent is evaporated in vacuo (260 Pa) at 50° C. Thus 33.2, g (99%) of title compound are obtained, which has higher purity than 95% by gas chromatographic analysis. Optionally the product can be purified by vacuum distillation (boiling temperature 85-86° C. at 1.3 Pa).

Workup

  1. additionare added
  2. additionare added to it dropwise in 10 minutes
  3. customthe solvent is evaporated in vacuo (260 Pa) at 50° C
  4. customare obtained
  5. distillationOptionally the product can be purified by vacuum distillation (boiling temperature 85-86° C. at 1.3 Pa)

Sources & evidence

ORD record
ord-e075880273fd4e359a62705cf3b09d0d
Source dataset
uspto-grants-2012_07
Patent number
US08217200B2

Reaction notes

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