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

HRID 2165810Notes

Reaction equation

HRID 2165810 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-])(=[O:15])=[O:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18].[K+].C(#N)C.CC(N(C)C)=O>O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([Cl:3])(=[O:15])=[O:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18]

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-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1250 ml of phosphorus oxychloride was added dropwise to a mixture comprising 1280 g of potassium 4-chloro-3-nitrobenzenesulfonate, 1150 ml of acetonitrile, 250 ml of sulforane and 30 ml of dimethylacetamide, while the inner temperature of the reaction system was kept at from 60° C. to 70° C. After being reacted for 3 hours at 73° C., the reaction mixture was cooled with water and 400 ml of water was gradually added thereto, and then the resulting mixture was poured into 5 liters of ice-water. The crystal precipitated was taken out by filtration, washed with water and dried. Yield: 1060 g, 84%.

Workup

  1. customwas kept at from 60° C. to 70° C
  2. customAfter being reacted for 3 hours at 73° C.
  3. additionwas gradually added
  4. customThe crystal precipitated
  5. filtrationwas taken out by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-84f1006622b840ac80ee8a5980bac4f2
Source dataset
uspto-grants-1990_07
Patent number
US04942114

Reaction notes

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