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

HRID 2073156Notes

Reaction equation

HRID 2073156 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.S1(CCCC1)(=O)=O.O(Cl)[Cl:27]>O.CC(N(C)C)=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

7

Reactant 4

HCID 6342AcetonitrileHCID 24646Chlorine monoxideHCID 31347SulfolaneHCID 81181Benzenesulfonic acid, 4-chloro-3-nitro-, potassium salt

Product 1

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

To a mixed solution containing 1,280 g of potassium 4-chloro-3-nitrobenzenesulfonate, 1,150 ml of acetonitrile, 250 ml of Sulfolane (tetrahydrothiophene 1,1-dioxide) and 30 ml of dimethylacetamide was dropwise added 1,250 ml of phoshporus oxychloride under an inside temperature at 60° C. to 70° C. After the reaction was continued for 3 hours at 73° C., the reaction mixture was cooled with water, and thereto was slowly added 400 ml of water. The thus obtained product was poured into 5 liters of ice-cold water. The crystalline precipitate was filtered off, washed with water, and dried.

Workup

  1. customat 60° C. to 70° C
  2. filtrationThe crystalline precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ec128a30c98840e18b7c5874721e8e87
Source dataset
uspto-grants-1990_04
Patent number
US04916047

Reaction notes

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