Dichloromethane → 3-Chloro-4-(chloromethyl)-1-prop-2-enylpyrrolidin-2-one

HRID 1111860Notes

Reaction equation

HRID 1111860 reaction equation
[CH2:1]([N:4]([CH2:10][CH:11]=[CH2:12])[C:5](=[O:9])[CH:6](Cl)[Cl:7])[CH:2]=[CH2:3].COCCOCCOC.C(Cl)[Cl:23]>>[CH2:1]([N:4]1[CH2:10][CH:11]([CH2:12][Cl:23])[CH:6]([Cl:7])[C:5]1=[O:9])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8150DiglymeHCID 37829Dichlormid

Product 1

HCID 132956733-Chloro-4-(chloromethyl)-1-prop-2-enylpyrrolidin-2-one

Procedure

Twenty and eight-tenths grams of N,N-diallyl dichloroacetamide was mixed with 25 g. of diethylene glycol dimethyl ether (diglyme), 1 g. of ferrous chloride (FeCl2.4H2O) added and the mixture was heated at reflux for 30 minutes. The conversion was monitored by the appearance of a new carbonyl peak at ~5.8 microns in the infrared. An additional gram of ferrous chloride (FeCl2.4H2O) was added and heating was continued for an additional 30 minutes. The reaction mixture was diluted with methylene chloride, washed with water and dried and stripped. The dark liquid product was distilled under vacuum to give 8.4 g. of light yellow oil, b.p. 124°-127° C. at 0.25 mm. nD30 1.4850.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. temperatureheating
  4. washwashed with water
  5. customdried
  6. distillationThe dark liquid product was distilled under vacuum
  7. customto give 8.4 g

Sources & evidence

ORD record
ord-9fedb49c30f64293990994ae3ba5cc19
Source dataset
uspto-grants-1978_10
Patent number
US04119636

Reaction notes

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