Aniline → N-phenylethene-1-sulfonamide

HRID 271242Notes

Reaction equation

HRID 271242 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.Cl[CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:2]1([NH:1][S:18]([CH:17]=[CH2:16])(=[O:20])=[O:19])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-

Product 1

HCID 12322399N-phenylethene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Aniline (0.98 mL, 10.7 mmol) and Et3N (1.8 mL, 12.9 mmol) in toluene (25 mL) were treated with 2-chloro-1-ethanesulfonylchloride (1.1 mL, 10.5 mmol). The exothermic reaction was stirred for 14 hours at room temperature. After stirring, the solution was diluted with EtOAc and washed with HCl (˜10% aq. soln.). The organic layer concentrated and purified via flash column chromatography (4:1 hexane/EtOAc) to afford two lots of phenyl(vinylsulfonyl)amine.

Workup

  1. customThe exothermic reaction
  2. stirringAfter stirring
  3. washwashed with HCl (˜10% aq. soln.)
  4. concentrationThe organic layer concentrated
  5. custompurified via flash column chromatography (4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-67e8cb5e915a4fa9a119b8f925cd448e
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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