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

HRID 1460810Notes

Reaction equation

HRID 1460810 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 962WaterSolvent2×

Procedure

To a mixture of 1280 g of potassium 4-chloro-3-nitrobenzenesulfonate, 1150 ml of acetonitrile, 250 ml of sulforan, and 30 ml of dimethylacetamide was added dropwise 1250 ml of phosphorus oxychloride so that the internal temperature was kept at 60° C. to 70° C. Then, after performing the reaction for 3 hours at 73° C., the reaction mixture was cooled with water and after adding slowly 400 ml of water thereto, the mixture was poured into 5 liters of ice-water. Crystals thus deposited were recovered by filtration, washed, and dried to provide 1060 g of the above-described compound with a yield of 84%. The melting point thereof was 55° C. to 56° C.

Workup

  1. customwas kept at 60° C. to 70° C
  2. customthe reaction for 3 hours at 73° C.
  3. filtrationCrystals thus deposited were recovered by filtration
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-c30c8aa5e905477381c911f39bcc35a0
Source dataset
uspto-grants-1991_12
Patent number
US05071994

Reaction notes

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