Water → HCID 135976149, compound

HRID 265371Notes

Reaction equation

HRID 265371 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[C:12]1[C:28]1[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=1)([OH:3])=[O:2].B(Br)(Br)Br.O>ClCCl>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:13]=[C:12]1[C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22916335HCID 22916335, compound

Product 1

HCID 135976149HCID 135976149, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(7-Carboxyheptyl)-2-(4-methoxyphenyl)-4,5-diphenyl-imidazole (2.5 g) was added, in portions over 40 minutes, to a solution of boron tribromide (2.17 ml) in anhydrous dichloromethane (40 ml). The reaction was stirred at room temperature for 5 h, cooled and water (50 ml) was carefully added. The organic layer was removed and the aqueous layer was washed with dichloromethane (3×75 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Column chromatography on silica gel eluted with a dichloro-methane:methanol gradient and recrystallisation from ethanol/water and acetonitrile gave 1-(7-carboxy-heptyl)-2-(4-hydroxyphenyl)-4,5-diphenyl-imidazole (0.49 g, 20%) as a white solid, m.p. 171°-172°. Further material was obtained from the mother liquors (0.79 g, 33%) m.p. 167°. Found C: 76.85; H, 6.65; N, 6.20%; C29H30N2O3 requires: C, 76.63; H, 6.65; N, 6.16%;

Workup

  1. temperaturecooled
  2. customThe organic layer was removed
  3. washthe aqueous layer was washed with dichloromethane (3×75 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated to dryness in vacuo
  6. washColumn chromatography on silica gel eluted with a dichloro-methane
  7. custommethanol gradient and recrystallisation from ethanol/water and acetonitrile

Sources & evidence

ORD record
ord-eb353a66fb28441a9c25eb8ffa8a27d4
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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