Aniline → 4'-Chloro-3'-phenylsulfamoylacetophenone

HRID 461181Notes

Reaction equation

HRID 461181 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].C(N(CC)CC)C.O1CCOCC1.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11](=[O:13])(=[O:12])[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 126197955-Acetyl-2-chlorobenzene-1-sulfonyl chloride

Product 1

HCID 227606124'-Chloro-3'-phenylsulfamoylacetophenone

Conditions

Temperature
60 °C

Procedure

12.6 g of 4'-chloro-3'-chlorosulfonylacetophenone were introduced, while stirring, in a mixture of 5.6 g of aniline, 7.5 g of triethyl amine and 100 ml of dioxane. The mixture was allowed to dwell over night at 20° C, it was heated to 60° C during 30 minutes while stirring and the separated triethylamine-hydrochloride was separated. The filtrate was concentrated under reduced pressure and the residue was crystallized under water. Colorless crystals (from isopropanol/active charcoal, melting point: 142° C.

Workup

  1. waitto dwell over night at 20° C
  2. customthe separated triethylamine-hydrochloride was separated
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was crystallized under water

Sources & evidence

ORD record
ord-c8e8779000324b1ca6cdfc4478c68f4d
Source dataset
uspto-grants-1977_12
Patent number
US04061761

Reaction notes

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