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

HRID 1086327Notes

Reaction equation

HRID 1086327 reaction equation
S(O[C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:21]2[CH:26]=[CH:25][C:24](OS(C)(=O)=O)=[C:23]([N+:32]([O-:34])=[O:33])[CH:22]=2)([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])=[CH:8][C:7]=1[N+:35]([O-:37])=[O:36])(C)(=O)=O.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(#N)C>[NH:38]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:21]2[CH:26]=[CH:25][C:24]([NH:32][C:23]3[CH:24]=[CH:25][CH:26]=[CH:21][CH:22]=3)=[C:23]([N+:32]([O-:34])=[O:33])[CH:22]=2)([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])=[CH:8][C:7]=1[N+:35]([O-:37])=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 142050422,2-Bis-(4-mesyloxy-3-nitrophenyl)-hexafluoropropane

Product 1

HCID 142050452,2-Bis-(4-anilino-3-nitrophenyl)-hexafluoropropaneYield 159.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 60 g (0.103 mol) of 2,2-bis-(4-mesyloxy-3-nitrophenyl)-hexafluoropropane and 122.8 g (1.32 mol) of aniline in 400 ml of acetonitrile is heated under reflux for 24 hours. In the course of this the methanesulfonic acid salt of aniline is precipitated, and is removed by filtration with suction. The filtrate is freed from the solvent and from excess aniline by distillation under reduced pressure. Recrystallizing the residue from ethanol gives 47.3 g of 2,2-bis-(4-anilino-3-nitrophenyl)-hexafluoropropane (80% yield). M.p. 165-166° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customIn the course of this the methanesulfonic acid salt of aniline is precipitated
  3. customis removed by filtration with suction
  4. distillationThe filtrate is freed from the solvent and from excess aniline by distillation under reduced pressure
  5. customRecrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-12c893f0a5424d7dafa1d8143455f13e
Source dataset
uspto-grants-1991_07
Patent number
US05028728

Reaction notes

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