Aniline → Phenylsulfamoyl chloride

HRID 1837133Notes

Reaction equation

HRID 1837133 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[C:7]1([NH:6][S:2]([Cl:1])(=[O:5])=[O:3])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 24638Chlorosulfonic acid

Product 1

HCID 11564615Phenylsulfamoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

25.2 g of chlorosulphonic acid are added slowly to a solution of 60.6 g of aniline in 316 ml of methylene chloride cooled to −5° C. When the addition is complete, the mixture is allowed to return to ambient temperature and the precipitate obtained is filtered off. After drying, the precipitate is taken up in 231 ml of toluene, and 45.1 g of phosphorus pentachloride are added gradually. The mixture is then refluxed for 3 hours 30 minutes and, after returning to ambient temperature, the precipitate formed is filtered off. The filtrate is concentrated to obtain the expected product.

Workup

  1. additionWhen the addition
  2. customto return to ambient temperature
  3. customthe precipitate obtained
  4. filtrationis filtered off
  5. customAfter drying
  6. addition45.1 g of phosphorus pentachloride are added gradually
  7. temperatureThe mixture is then refluxed for 3 hours 30 minutes
  8. customafter returning to ambient temperature
  9. customthe precipitate formed
  10. filtrationis filtered off
  11. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-a49acfacb72043fc8c3a419c23131692
Source dataset
uspto-grants-2004_08
Patent number
US06780868B2

Reaction notes

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