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5-Cyano-7-(3-hydroxymethylphenyl)-1-phenylbenzimidazole → 5-Cyano-7-(4-hydroxyphenyl)-1-phenylbenzimidazole

HRID 644516
Notes
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Reaction equation

HRID 644516 reaction equation
[C:1]([C:3]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22]C=[C:20]([CH2:24][OH:25])[CH:19]=2)[C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2]>C(#N)C>[C:1]([C:3]1[CH:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:24]([OH:25])=[CH:22][CH:23]=2)[C:6]2[N:7]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 113931985-Cyano-7-(3-hydroxymethylphenyl)-1-phenylbenzimidazole

Product 1

HCID 112669215-Cyano-7-(4-hydroxyphenyl)-1-phenylbenzimidazoleYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This was prepared in a similar manner to 5-cyano-7-(3-hydroxymethylphenyl)-1-phenylbenzimidazole, with 90 h reflux before removal of solvent using nitrogen to give an oily residue. The residue was taken up in acetonitrile (3 ml) and the resulting solid filtered off and dried under reduced pressure to give the desired product (490 mg, 77%) m/z, 312.3 (M+H)+.

Workup

  1. temperature
reflux before removal of solvent
  • customto give an oily residue
  • filtrationthe resulting solid filtered off
  • customdried under reduced pressure
  • Sources & evidence

    ORD record
    ord-373521223c4d4d638f2f9a5392e83ecb
    Source dataset
    uspto-grants-2010_04
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US07700638B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes