Water → HCID 22916451, compound

HRID 265386Notes

Reaction equation

HRID 265386 reaction equation
B(Br)(Br)Br.[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=2)=[C:18]([C:28]2[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=2)[N:17]=[C:16]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([OH:7])=[O:6].O>ClCCl>[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[C:18]([C:28]2[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=2)[N:17]=[C:16]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromide2×HCID 22916442HCID 22916442, compound

Product 1

HCID 22916451HCID 22916451, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.7 ml) was added to a suspension of 1-(7-carboxyheptyl)-4,5-bis(4-methoxyphenyl)-2-phenylimidazole (0.7 g) in anhydrous dichloromethane (20 ml) and the reaction was stirred at room temperature for 1 h. Boron tribromide (0.3 ml) was added and the reaction was stirred at reflux for 2 h and at room temperature for 20 h. Water was carefully added to the cooled reaction mixture and the resulting yellow precipitate was collected. Column chromatography on silica gel eluted with a dichloromethane:methanol gradient and recrystallisation from ethanol and water gave 1-(7-carboxyheptyl)-4,5-bis-(4-hydroxyphenyl)-2-phenylimidazole (0.44 g, 67%) as a cream solid, m.p 135°-7°; Found C, 73.97; H, 6.38; N, 5.98%; C29H30N2O4 requires: C, 74.02; H, 6.42; N, 5.95%.

Workup

  1. stirringthe reaction was stirred
  2. temperatureat reflux for 2 h and at room temperature for 20 h
  3. customthe resulting yellow precipitate was collected
  4. washColumn chromatography on silica gel eluted with a dichloromethane
  5. custommethanol gradient and recrystallisation from ethanol and water

Sources & evidence

ORD record
ord-96ea498095ad4be8a121d38918ed4ed2
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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