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

HRID 2165033Notes

Reaction equation

HRID 2165033 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+].P(Cl)(Cl)([Cl:18])=O.O>C(#N)C.S1(CCCC1)(=O)=O.CC(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([Cl:18])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 3

HCID 962Water2×HCID 24813Phosphorus oxychlorideHCID 81181Benzenesulfonic acid, 4-chloro-3-nitro-, potassium salt

Product 1

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

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 31347SulfolaneSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution mixture of 1,280 g of potassium 4-chloro-3-nitrobenzenesulfonate in 1,150 ml of acetonitrile, 250 ml of sulfolane and 30 ml of dimethylacetamide was added dropwise 1,250 ml of phosphorus oxychloride while the temperature was kept at 60° to 70° C. After the reaction proceeded for 3 hours at 73° C., the reaction mixture was cooled with water, then 400 ml of water was added thereto gradually, and then 5 liters of ice water was poured into the reaction mixture. The deposited crystals were filtered followed by washing with water and drying.

Workup

  1. customwas kept at 60° to 70° C
  2. filtrationThe deposited crystals were filtered
  3. washby washing with water
  4. customdrying

Sources & evidence

ORD record
ord-9081fd0728b34433930572bc9c05281c
Source dataset
uspto-grants-1990_07
Patent number
US04939066

Reaction notes

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