Dimethylformamide → Permethric chloride

HRID 905321Notes

Reaction equation

HRID 905321 reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][CH:4]1[CH:6]([C:7](O)=[O:8])[C:5]1([CH3:11])[CH3:10].CN(C)C=O.S(Cl)([Cl:20])=O>C(Cl)Cl>[Cl:1][C:2]([Cl:12])=[CH:3][CH:4]1[CH:6]([C:7]([Cl:20])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 91658Permethric acid

Product 1

HCID 94551Permethric chlorideYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid (32.0 grams) was stirred in 400 ml of methylene chloride under nitrogen. To this was added N,N-dimethylformamide (12 ml) and thionyl chloride (22.6 grams). The resulting solution was heated at reflux temperature for about 1.5 hours. The solvent was then removed in vacuo leaving about 36 grams of the desired 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxoyl chloride, which was confirmed by IR and NMR spectroscopy.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux temperature for about 1.5 hours
  3. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-8ef6ad0f0b9f4b93916da5eb8744202b
Source dataset
uspto-grants-1983_12
Patent number
US04423222

Reaction notes

Loading…