Phosphorus oxychloride → 2-Chloro-5-nitrobenzenesulfonyl chloride

HRID 375675

Reaction equation

HRID 375675 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([O-:14])(=O)=[O:12].[Na+].S1(CCCC1)(=O)=O.P(Cl)(Cl)([Cl:25])=O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([Cl:25])(=[O:14])=[O:12]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31347SulfolaneHCID 70350Benzenesulfonic acid, 2-chloro-5-nitro-, sodium salt (1:1)

Product 1

HCID 206302-Chloro-5-nitrobenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 104 g of commercially available sodium 2-chloro-5-nitrobenzenesulfonate, 200 ml of acetonitrile and 200 ml of sulfolane stirred at 25° C., was added 153 ml of phosphorus oxychloride over a period of 30 minutes. The temperature was not allowed to exceed 40° C. After completion of the addition, the reaction mixture was heated to 70° C. for 1.5 hours. On cooling to 0° C., the reaction mixture was poured over ice. The resulting solid product was washed with cold water, filtered and air-dried to give 77.6 g of the title compound with a melting point of 87°-89° C.

Workup

  1. customto exceed 40° C
  2. additionAfter completion of the addition
  3. temperaturethe reaction mixture was heated to 70° C. for 1.5 hours
  4. temperatureOn cooling to 0° C.
  5. additionthe reaction mixture was poured over ice
  6. washThe resulting solid product was washed with cold water
  7. filtrationfiltered
  8. customair-dried

Sources & evidence

ORD record
ord-d54bc8b308fa4f97afa0bc5e95f44a26
Source dataset
uspto-grants-1996_01
Patent number
US05486610

Linked notes

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