Water → 4-Nitrobenzenesulfonyl chloride

HRID 2394932Notes

Reaction equation

HRID 2394932 reaction equation
CS[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.O.[S:13]([Cl:17])(Cl)(=[O:15])=[O:14]>ClC1C=CC=CC=1>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([S:13]([Cl:17])(=[O:15])=[O:14])=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 961094-Nitrophenyl methyl sulfide

Product 1

HCID 74044-Nitrobenzenesulfonyl chlorideYield 95.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
10 °C

Procedure

A 2-liter, 4-necked flask equipped with a stirrer, thermometer, condenser and a dropping funnel having a by-pass was charged with 20.4 g (0.10 mole) of 4-nitrophenyl methyl sulfide, 10 g of water and 200 g of monochlorobenzene. Then, 94.5 g (0.70 mole) of sulfuryl chloride was added dropwise at 10° C. over a period of about 2 hours. Thereafter the mixture was stirred at 10° C. for 6 hours to complete the reaction. After completion of the reaction, the oil layer was separated and 10 g of water was added to accomplish washing. Then, the oil layer was separated and left to stand for about 1 hour with the addition of about 5 g of anhydrous sodium sulfate to remove the water. The solvent was distilled off to give crude crystals. The crude crystals were dissolved in monochlorobenzene and a poor solvent was added for recrystallization, giving 21.1 g of 4-nitrobenzenesulfonyl chloride as white crystals in a yield of 95% as calculated based on 4-nitrophenyl methyl sulfide.

Workup

  1. customA 2-liter, 4-necked flask equipped with a stirrer
  2. customthermometer, condenser and a dropping funnel having
  3. customthe reaction
  4. customAfter completion of the reaction
  5. customthe oil layer was separated
  6. addition10 g of water was added
  7. washto accomplish washing
  8. customThen, the oil layer was separated
  9. waitleft
  10. additionto stand for about 1 hour with the addition of about 5 g of anhydrous sodium sulfate
  11. customto remove the water
  12. distillationThe solvent was distilled off
  13. customto give crude crystals
  14. additiona poor solvent was added for recrystallization

Sources & evidence

ORD record
ord-5f236e35a596452fbd6e645cf373848e
Source dataset
uspto-grants-1998_09
Patent number
US05811571

Reaction notes

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