Sodium Hydroxide → 2-[4-(3-Bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylic acid

HRID 1181313Notes

Reaction equation

HRID 1181313 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:15]3[CH:23]=[CH:24][C:25]([C:27]([O:29]CC)=[O:28])=[CH:26][C:14]=3[N:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+]>O1CCCC1.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:15]3[CH:23]=[CH:24][C:25]([C:27]([OH:29])=[O:28])=[CH:26][C:14]=3[N:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9914616Ethyl 2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

Product 1

HCID 102067052-[4-(3-Bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[4-(3-bromophenoxy)phenyl]-1-cyclohexyl-benzimidazole-5-carboxylate (1.0 g) obtained in Example 1 was dissolved in tetrahydrofuran (10 ml) and ethyl alcohol (10 ml), and 4N sodium hydroxide (10 ml) was added. The mixture was refluxed under heating for 1 hr. The reaction mixture was concentrated under reduced pressure and water was added to the residue. The mixture was acidified with 6N hydrochloric acid and the precipitated crystals were collected by filtration to give the title compound (0.9 g, yield 96%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure and water
  4. additionwas added to the residue
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-9945308b5c234ab7a5dc95c043624e11
Source dataset
uspto-grants-2007_10
Patent number
US07285551B2

Reaction notes

Loading…