Dichloromethane → 2-Pyrrolidinone, 3-chloro-4-(chloromethyl)-1-(phenylmethyl)-

HRID 1834109Notes

Reaction equation

HRID 1834109 reaction equation
[CH2:1]([N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[O:9])[CH:6](Cl)[Cl:7])[CH:2]=[CH2:3].COCCOCCOC.N1CCCC1=O.C(Cl)[Cl:33]>>[CH2:10]([N:4]1[CH2:1][CH:2]([CH2:3][Cl:33])[CH:6]([Cl:7])[C:5]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8150DiglymeHCID 120252-PyrrolidoneHCID 10083827Acetamide, 2,2-dichloro-N-(phenylmethyl)-N-2-propenyl-

Product 1

HCID 118212562-Pyrrolidinone, 3-chloro-4-(chloromethyl)-1-(phenylmethyl)-

Procedure

Eleven and one-tenth grams of N-allyl-N-benzyl dichloroacetamide was dissolved in 12 ml. of diglyme and 1 g. of anhydrous ferrous chloride added. The mixture was heated at reflux under nitrogen until conversion to the pyrrolidinone was complete as indicated by GLPC. The mixture was diluted with methylene chloride, washed with 5 per cent hydrochloric acid, separated, dried over anhydrous magnesium sulfate, treated with activated carbon and Florisil and stripped under vacuum. Yield was 6 g. of the title compound, nD30 1.5387.

Workup

  1. temperatureThe mixture was heated
  2. washwashed with 5 per cent hydrochloric acid
  3. customseparated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additiontreated with activated carbon and Florisil

Sources & evidence

ORD record
ord-6ec93fadb1a84c53ada798b7bce2a59a
Source dataset
uspto-grants-1978_01
Patent number
US04069038

Reaction notes

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