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

HRID 644516Notes

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]

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. temperaturereflux before removal of solvent
  2. customto give an oily residue
  3. filtrationthe resulting solid filtered off
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-373521223c4d4d638f2f9a5392e83ecb
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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