Dimethylformamide → 5-Acetyl-2-methylbenzene-1-sulfonyl chloride

HRID 2166215Notes

Reaction equation

HRID 2166215 reaction equation
C(N(CC)C1C=CC=CC=1)C.[C:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:25])=[C:19]([S:21](O)(=[O:23])=[O:22])[CH:20]=1)(=[O:14])[CH3:13].CN(C)C=O.S(Cl)([Cl:33])=O>C(Cl)(Cl)Cl.O>[C:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:25])=[C:19]([S:21]([Cl:33])(=[O:23])=[O:22])[CH:20]=1)(=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7061N,N-DiethylanilineHCID 24386Thionyl ChlorideHCID 132542755-Acetyl-2-methylbenzene-1-sulfonic acid

Product 1

HCID 126197945-Acetyl-2-methylbenzene-1-sulfonyl chlorideYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

363 Grams (1.0M) of N,N-diethylaniline salt of 5-acetyl-2-methylbenzenesulfonic acid was dissolved in 934 g of chloroform, to this solution was added a mixture of 80.3 g (1.1M) of N,N-dimethylformamide with 130.9 g (1.1M) of thionyl chloride at a temperature of 2°-3° C., and the whole mixture was stirred at the same temperature for 1 hour. 1,500 Grams of water was added to this reaction mixture, the chloroform layer was separated and washed 3 times with 500 g of water. The chloroform layer was concentrated to obtain 203.1 g (0.874M) of 5-acetyl-2-methylbenzenesulfonyl chloride. The yield was 87.4% on the basis of N,N-diethylaniline salt of 5-acetyl-2-methylbenzenesulfonate.

Workup

  1. additionwas added
  2. customthe chloroform layer was separated
  3. washwashed 3 times with 500 g of water
  4. concentrationThe chloroform layer was concentrated

Sources & evidence

ORD record
ord-be50d02b3a2c4bab96e5e81da647b30d
Source dataset
uspto-grants-1990_07
Patent number
US04943655

Reaction notes

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