Aniline → 2,2-Bis-(4-anilino-3-nitrophenyl)-hexafluoropropane

HRID 1086328Notes

Reaction equation

HRID 1086328 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:21]([C:30]2[CH:35]=[CH:34][C:33](OS(C3C=CC(C)=CC=3)(=O)=O)=[C:32]([N+:47]([O-:49])=[O:48])[CH:31]=2)([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])[CH:7]=[CH:8][C:9]=1OS(C1C=CC(C)=CC=1)(=O)=O)([O-:3])=[O:2].[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C(#N)C>[NH:50]([C:33]1[CH:34]=[CH:35][C:30]([C:21]([C:6]2[CH:7]=[CH:8][C:9]([NH:1][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)([C:26]([F:28])([F:29])[F:27])[C:22]([F:25])([F:23])[F:24])=[CH:31][C:32]=1[N+:47]([O-:49])=[O:48])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 142050432,2-Bis-(3-nitro-4-tosyloxyphenyl)hexafluoropropane

Product 1

HCID 142050452,2-Bis-(4-anilino-3-nitrophenyl)-hexafluoropropaneYield 218.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In an alternative procedure, 7.3 g (0.01 mol) of 2,2-bis-(3-nitro-4-tosyloxyphenyl)-hexafluoropropane, 11.6 g (0.125 mol) of aniline and 50 ml of acetonitrile are heated under reflux for 24 hours. After the red-orange suspension has been cooled, the solid is removed and washed with acetonitrile. The solvent is removed from the filtrate, and the product is recrystallized twice from ethanol to give 6.3 g of 2,2-bis-(4-anilino-3-nitrophenyl)-hexafluoropropane (65% yield).

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureAfter the red-orange suspension has been cooled
  3. customthe solid is removed
  4. washwashed with acetonitrile
  5. customThe solvent is removed from the filtrate
  6. customthe product is recrystallized twice from ethanol

Sources & evidence

ORD record
ord-da97e63ab5284f3480f4485657d21396
Source dataset
uspto-grants-1991_07
Patent number
US05028728

Reaction notes

Loading…