4-Chloroaniline → HCID 21313260, compound

HRID 971647Notes

Reaction equation

HRID 971647 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]([S:14](Cl)(=[O:16])=[O:15])=[C:11]([Cl:13])[Cl:12]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:14]([C:10]([Cl:9])=[C:11]([Cl:13])[Cl:12])(=[O:16])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 20192682HCID 20192682, compound

Product 1

HCID 21313260HCID 21313260, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 7.6 g (0.06 mol) p-chloroaniline and 7.0 g (0.03 mol) trichlorovinylsulfonyl chloride in 150 ml chloroform was heated under reflux for 3 hours. The reaction mixture was then cooled, washed with water, dried over magnesium sulfate and evaporated to give an oily residue. The residue was chromatographed on silica gel. N-(p-chlorophenyl)trichlorovinylsulfonamide, m.p. 73°-76° C., was eluted from the silica gel with 30% ether-70% hexane. Elemental analysis for C8H5Cl4NO2S showed: calculated, %S, 9.99, %Cl 44.2; found, %S, 10.1, %Cl 48.2.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureThe reaction mixture was then cooled
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give an oily residue
  7. customThe residue was chromatographed on silica gel
  8. washN-(p-chlorophenyl)trichlorovinylsulfonamide, m.p. 73°-76° C., was eluted from the silica gel with 30% ether-70% hexane

Sources & evidence

ORD record
ord-3fea5737799040119d56392efdbac867
Source dataset
uspto-grants-1979_07
Patent number
US04160845

Reaction notes

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