Acetic Acid → Phenol, 4,4'-(2-phenyl-1H-imidazole-4,5-diyl)bis-

HRID 1197024Notes

Reaction equation

HRID 1197024 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(O)(=O)C.Br.[OH-].[Na+]>O>[OH:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]2[N:12]=[C:11]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 11022141H-imidazole, 2-phenyl-4,5-bis(4-methoxyphenyl)-

Product 1

HCID 10892800Phenol, 4,4'-(2-phenyl-1H-imidazole-4,5-diyl)bis-Yield 79.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,5-Bis(4-methoxyphenyl)-2-phenylimidazole (15.8 g, 0.044 mol) was placed in a 250 ml three neck round bottom flask equipped with a mechanical stirrer, nitrogen inlet, thermometer, reflux condenser and hydrogen bromide gas trap along with acetic acid (75 ml) and 47-49% aqueous hydrogen bromide solution (130 ml). The mixture was heated to reflux for 16 hours, cooled, poured into water to give a white solid, which was neutralized with sodium hydroxide, collected, washed with water and dried at 100° C. Yield was 13.7 g of white solid. Recrystallization from ethanol/water (3:1) gave 11.5 g (79%) of white crystals, m.p. 327°-330° C. Anal. Calcd. for C21H16N2O2 : C, 76.80%; H, 4.91%; N, 8.53%. Found: C, 76.50%; H, 5.00%; N, 8.44%.

Workup

  1. customequipped with a mechanical stirrer, nitrogen inlet
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 16 hours
  4. temperaturecooled
  5. customto give a white solid, which
  6. customcollected
  7. washwashed with water
  8. customdried at 100° C
  9. customRecrystallization from ethanol/water (3:1)

Sources & evidence

ORD record
ord-0a4bfd3b5ff24c7089e80960b06594ad
Source dataset
uspto-grants-1992_05
Patent number
US05116934

Reaction notes

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