Bifonazole → 1,3-Bis-[alpha-(-biphenylyl)-benzyl]-imidazolium chloride

HRID 1389057

Reaction equation

HRID 1389057 reaction equation
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([CH:7]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[C:25]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]([Cl:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C>[Cl-:38].[C:25]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]([N+:16]1[CH:17]=[CH:18][N:14]([CH:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:15]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 2378BifonazoleHCID 13823625alpha-Biphenylyl-benzyl chloride

Product 1

HCID 202982001,3-Bis-[alpha-(-biphenylyl)-benzyl]-imidazolium chlorideYield 122.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

31 g (0.1 mol) of 1-[α-(4-biphenylyl)-benzyl]-imidazole and 27.9 g (0.1 mol) of α-biphenylyl-benzyl chloride are suspended in 200 ml of acetonitrile. The mixture is heated under reflux for 18 hours. The reaction mixture is then concentrated by distilling off the solvent and the residue, in 500 ml of toluene, is heated under reflux. The gel thereby formed is separated off and caused to crystallise by trituration with diisopropyl ether. 36 g (62% of theory) of 1,3-bis-[α-(-biphenylyl)-benzyl]-imidazolium chloride of melting point 150° C. (with decomposition) are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe reaction mixture is then concentrated
  4. distillationby distilling off the solvent
  5. temperaturethe residue, in 500 ml of toluene, is heated
  6. temperatureunder reflux
  7. customThe gel thereby formed
  8. customis separated off
  9. customto crystallise by trituration with diisopropyl ether

Sources & evidence

ORD record
ord-b2e8f8b42a1d4840979c37d9bd326313
Source dataset
uspto-grants-1981_01
Patent number
US04243670

Linked notes

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