Aniline → N-[2,2-bis(benzenesulfonyl)ethenyl]aniline

HRID 542888Notes

Reaction equation

HRID 542888 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:11]=[C:12]([S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23])[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])C>C(O)C>[C:2]1([NH:1][CH:11]=[C:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])[S:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 124009381,1-Bis(phenylsulphonyl)-2-ethoxyethene

Product 1

HCID 2142012N-[2,2-bis(benzenesulfonyl)ethenyl]anilineYield 80.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of aniline (1.0 g) and 2-ethoxy-1,1-bis(phenylsulphonyl)ethene (3.5 g) was heated at 160°-180° C. for 30 minutes, allowing any ethanol evolved to escape. After cooling, the residue was recrystallised by dissolving in a minimum of hot choroform and diluting with between 3 and 4 volumes of ethanol to give 1-phenylamino-2,2-bis(phenylsulphonyl)ethene (3.2 g), m.p. 199°-202° C.

Workup

  1. temperaturewas heated at 160°-180° C. for 30 minutes
  2. temperatureAfter cooling
  3. customthe residue was recrystallised
  4. dissolutionby dissolving in a minimum of hot choroform
  5. additiondiluting with between 3 and 4 volumes of ethanol

Sources & evidence

ORD record
ord-01d22cee2834498595f468972f2593d5
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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