Thionyl Chloride → 2-Methyl-4,5-di(methylsulfonyl)benzoyl chloride

HRID 1838678Notes

Reaction equation

HRID 1838678 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][S:6]([C:9]1[C:17]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([CH3:22])[CH:10]=1)(=[O:8])=[O:7]>CN(C=O)C>[CH3:5][S:6]([C:9]1[C:17]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][C:12]([C:13]([Cl:3])=[O:14])=[C:11]([CH3:22])[CH:10]=1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11266313HCID 11266313, compound

Product 1

HCID 110882142-Methyl-4,5-di(methylsulfonyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15 l of thionyl chloride are initially introduced at 40°, and 50 ml of DMF are added. 3.8 kg of 4,5-bismethanesulfonyl-2-methylbenzoic acid are slowly introduced with stirring, and the mixture is then stirred at the boiling point for 1 hour. After cooling, the excess SOCl2 is removed, and the residue is codistilled a number of times with 5 l of toluene, giving 4, 5-bismethanesulfonyl-2-methylbenzoyl chloride, which is reacted further as the crude product.

Workup

  1. stirringthe mixture is then stirred at the boiling point for 1 hour
  2. temperatureAfter cooling
  3. customthe excess SOCl2 is removed

Sources & evidence

ORD record
ord-ee33cefa89264912ba9eb28eb36340f3
Source dataset
uspto-grants-2004_01
Patent number
US06673968B1

Reaction notes

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