Acetonitrile → Benzenesulfonyl chloride, 4-chloro-3-nitro-

HRID 1460418Notes

Reaction equation

HRID 1460418 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[K+].C(#N)C.CC(N(C)C)=O.P(Cl)(Cl)([Cl:27])=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([Cl:27])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 81181Benzenesulfonic acid, 4-chloro-3-nitro-, potassium salt

Product 1

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-Yield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution consisting of 1,280 g of potassium 4-chloro-3 nitrobenzenesulfonate, 1,150 ml of acetonitrile, 250 ml of sulforan, and 30 ml of dimethylacetamide, was added dropwise 1,250 ml of phosphorous oxychloride, while maintaining the inner temperature between 60° C. and 70° C. The mixture was allowed to react at 73° C. for 3 hours. After allowing to cool, 400 ml of water was slowly added thereto, and the reaction mixture was poured into 5l of ice-water. The crystals thus precipitated were filtered, washed with water, and dried to obtain 1,060 g (84%) of the noted compound.

Workup

  1. temperaturewhile maintaining the inner temperature between 60° C. and 70° C
  2. customto react at 73° C. for 3 hours
  3. temperatureto cool
  4. customThe crystals thus precipitated
  5. filtrationwere filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b870061e36bc4173a835dcba868b16d0
Source dataset
uspto-grants-1991_12
Patent number
US05071729

Reaction notes

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