Thionyl Chloride → HCID 11289887, compound

HRID 460505Notes

Reaction equation

HRID 460505 reaction equation
[CH3:1][C:2]1[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[C:9]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:21])=O>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[C:9]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:21])=[O:5]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 18446116HCID 18446116, compound

Product 1

HCID 11289887HCID 11289887, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

A few drops of dimethylformamide were added to a solution of 63 g (0.22 mol) of 2-methyl-3,4-di(methylsulfonyl)benzoic acid in 550 ml of toluene, and 36 g (0.3 mol) of thionyl chloride were then added dropwise. The reaction mixture was heated at reflux for 1.5 hours. After cooling, the reaction mixture was concentrated. This gave 62 g (93% yield) of 2-methyl-3,4-di(methylsulfonyl)benzoyl chloride as a beige solid.

Workup

  1. additionwere then added dropwise
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1.5 hours
  4. temperatureAfter cooling
  5. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-b5f5a2e50812405eb072fa45585cbf95
Source dataset
uspto-grants-2007_03
Patent number
US07196229B2

Reaction notes

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