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

HRID 727734Notes

Reaction equation

HRID 727734 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.S1(CCCC1)(=O)=O>O.CC(N(C)C)=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

7

Reactant 4

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 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

1,250 ml of phosphorus oxychloride was added dropwise to a mixture of 1,280 g of potassium 4-chloro-3-nitrobenzenesulfonate, 1,150 ml of acetonitrile, 250 ml of sulfolane, and 30 ml of dimethylacetamide in such a manner that the internal temperature thereof was kept at 60° to 70° C. After being allowed to react at a temperature of 73° C. for 3 hours, the reaction mixture was cooled with water, and 400 ml of water was gradually added to the reaction mixture. The cooled reaction mixture was then added to 5 l of ice water. The resulting crystals were filtered off, washed with water, and then dried. (Yield: 1,060 g (84%); m.p.: 55°-56° C.)

Workup

  1. customthereof was kept at 60° to 70° C
  2. customto react at a temperature of 73° C. for 3 hours
  3. additionwas gradually added to the reaction mixture
  4. customThe cooled reaction mixture
  5. filtrationThe resulting crystals were filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-491dd25abc4b416488af1c90a78af4aa
Source dataset
uspto-grants-1991_09
Patent number
USH0000963

Reaction notes

Loading…