N-Phenyl-o-phenylenediamine → 2-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazole

HRID 604238Notes

Reaction equation

HRID 604238 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1>>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 68297N-Phenyl-o-phenylenediamineHCID 707414-Bromobenzaldehyde

Product 1

HCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazole

Procedure

To a flask containing N-phenyl-o-phenylenediamine (9.21 g, 50 mmol) and 4-bromobenzaldehyde (9.25 g, 50 mmol) was added 50 mL of 20-methoxyethanol. After the mixture was refluxed for 48 h, the volatile was removed under vacuum and the residue was extracted with CH2Cl2. The organic extract was washed with brine, dried over anhydrous MgSO4, filtered and pumped dry. The crude product was purified by column chromatography using a mixture of CH2Cl2 and n-hexane (1:1 by vol.) as the eluent. Analytically pure 2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole was isolated as a white solid in 72% (9.77 g) yield. 1H NMR (400 MHz, CDCl3): δ 7.68 (d, 1 H, J=8.0 Hz), 7.35-7.29 (m, 4 H), 7.24-7.20 (m, 1 H), 7.15-7.02 (m, 7 H). MS (FAB): m/z 348.9 (M+). Anal. calcd. for C19H13BrN2: C, 65.35; H, 3.75; N, 8.02. Found: C, 65.22; H, 3.78; N, 8.01.

Workup

  1. temperatureAfter the mixture was refluxed for 48 h
  2. customthe volatile was removed under vacuum
  3. extractionthe residue was extracted with CH2Cl2
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. custompumped dry
  9. customThe crude product was purified by column chromatography
  10. additiona mixture of CH2Cl2 and n-hexane (1:1 by vol.) as the eluent

Sources & evidence

ORD record
ord-4da01a4208d34ed490387f466425946d
Source dataset
uspto-grants-2011_03
Patent number
US07910228B2

Reaction notes

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