2-Methoxyethanol → 2,2-Dichloro-N-[(2-methoxyethoxy)methyl]-N-(prop-2-en-1-yl)acetamide

HRID 1905557Notes

Reaction equation

HRID 1905557 reaction equation
[CH2:1]([N:4]([CH2:10]Cl)[C:5](=[O:9])[CH:6]([Cl:8])[Cl:7])[CH:2]=[CH2:3].[CH3:12][O:13][CH2:14][CH2:15][OH:16].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:4]([CH2:10][O:16][CH2:15][CH2:14][O:13][CH3:12])[C:5](=[O:9])[CH:6]([Cl:8])[Cl:7])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 8471TriethylamineHCID 200358422,2-Dichloro-N-(chloromethyl)-N-(prop-2-en-1-yl)acetamide

Product 1

HCID 138242772,2-Dichloro-N-[(2-methoxyethoxy)methyl]-N-(prop-2-en-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-allyl-N-chloromethyldichloroacetamide (21.7 g., 0.1 mole) and 2-methoxyethanol (8.4 g., 8.7 ml., 0.11 mole) in dry chloroform (50 ml.) is placed in a round-bottomed, four-necked flask of 250 ml, equipped with a calcium chloride tube, reflux condenser, mechanical stirrer, dropping funnel and thermometer. Triethylamine (10.1g., 13.9 ml., 0.1 mole) is added under stirring and external cooling in such a rate that the temperature does not exceed 35° C. After the addition is complete, the mixture is stirred for an additional 2 hours at room temperature. The mixture is washed with water (2×70 ml) for removing the triethylamine hydrochloride formed, the chloroform solution is dried over anydrous sodium sulfate and, after distillation of the chloroform, the product is dried under reduced pressure to give 23.6 g. (92%) of a pale yellow oil which is the named compound of 95% purity according to an analysis by gas chromatography; nD25 =1.4801. This product is directly useful for practical purposes.

Workup

  1. customequipped with a calcium chloride tube
  2. temperaturereflux condenser, mechanical stirrer
  3. temperatureexternal cooling in such a rate that the temperature
  4. customdoes not exceed 35° C
  5. additionAfter the addition
  6. stirringthe mixture is stirred for an additional 2 hours at room temperature
  7. washThe mixture is washed with water (2×70 ml)
  8. customfor removing the triethylamine hydrochloride
  9. customformed
  10. dry with materialthe chloroform solution is dried over anydrous sodium sulfate
  11. distillationafter distillation of the chloroform
  12. customthe product is dried under reduced pressure
  13. customto give 23.6 g

Sources & evidence

ORD record
ord-a8c2c8904af94438aff2f0857934eafb
Source dataset
uspto-grants-1989_06
Patent number
US04843177

Reaction notes

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