Sodium Hydroxide → Ethyl 1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylate

HRID 1835576

Reaction equation

HRID 1835576 reaction equation
BrC1C=C(C=CC=1)O[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][CH2:30][CH3:31])=[O:28])=[CH:26][C:14]=3[N:13]=2)=[CH:8][CH:7]=1.[C:35]1(/[CH:43]=[CH:44]/C2C=CC=CC=2)[CH:40]=[CH:39][C:38](C=O)=[CH:37][CH:36]=1.C1C=CC2C(=NO[N+]=2[O-])C=1.[OH-].[Na+]>CO.C(#N)C.C(OCC)(=O)C>[CH:17]1([N:16]2[C:15]3[CH:23]=[CH:24][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:26][C:14]=3[N:13]=[C:12]2[C:9]2[CH:10]=[CH:11][C:6](/[CH:44]=[CH:43]/[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:7][CH:8]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 68075BenzofuroxanHCID 53758764-Formyl-trans-stilbeneHCID 9914616Ethyl 2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

Product 1

HCID 10114855Ethyl 1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylateYield 124.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-amino-4-cyclohexylaminobenzoate (500 mg) obtained in Example 1, Step 3, was dissolved in methyl alcohol (6 ml) and trans-4-stilbenecarbaldehyde (397 mg) was added under ice-cooling. The mixture was stirred overnight at room temperature. The reaction mixture was ice-cooled and benzofuroxan (259 mg) dissolved in acetonitrile (2 ml) was added. The mixture was stirred for 7 hr at 50° C. The reaction mixture was ice-cooled. After 1N sodium hydroxide was added, ethyl acetate was added and the mixture was extracted. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (developing solvent, n-hexane:ethyl acetate=4:1) to give the title compound (540 mg, yield 63%).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. additionwas added
  4. stirringThe mixture was stirred for 7 hr at 50° C
  5. temperaturecooled
  6. extractionthe mixture was extracted
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel flash chromatography (developing solvent, n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-5eb0f9cc10374bbb97e33d09a992bb97
Source dataset
uspto-grants-2004_08
Patent number
US06770666B2

Linked notes

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