2-Phenylbenzimidazole → 1-Methyl-2-phenylbenzimidazole

HRID 1358702

Reaction equation

HRID 1358702 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]1CCN2C(=NCCC2)CC1>>[CH3:16][N:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 128552-PhenylbenzimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 758071-Methyl-2-phenylbenzimidazole

Conditions

Temperature
90 °C

Procedure

To a mixture of 2-phenylbenzimidazole (1.02 g, 5.25 mmol) in DMC (10 mL), DBU (0.80 g, 5.25 mmol) was added and the resulting mixture was heated to reflux (90° C.) for 6 hours. The solvent was evaporated under vacuum and the resulting oil was dissolved in methylene chloride (2 mL) and filtered through silica gel (2:1 EtOA/hexane). The solvent was evaporated under vacuum to afford 1-methyl-2-phenylbenzimidazole as a solid. The yield of 1-methyl-2-phenylbenzimidazole as determined by HPLC analysis was 98%.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated
  3. customThe solvent was evaporated under vacuum
  4. dissolutionthe resulting oil was dissolved in methylene chloride (2 mL)
  5. filtrationfiltered through silica gel (2:1 EtOA/hexane)
  6. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-c498807fa1ea4e88ac9ab9ba21af462a
Source dataset
uspto-grants-2003_07
Patent number
US06596877B2

Linked notes

Loading…