3-Amino-4-(cyclohexylamino)benzonitrile → 2-[4-Hydroxyphenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

HRID 392959Notes

Reaction equation

HRID 392959 reaction equation
Cl.[OH:2][C:3]1[CH:13]=[CH:12][C:6]([C:7](=N)OCC)=[CH:5][CH:4]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:18]#[N:19]>CO>[OH:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]2[N:23]([CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[C:22]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=3[N:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 226608193-Amino-4-(cyclohexylamino)benzonitrileHCID 135442973Ethyl 4-hydroxybenzimidate hydrochloride

Product 1

HCID 1356740912-[4-Hydroxyphenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrileYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 4-hydroxybenzimidate hydrochloride (5, 1.26 g, 6.7 mmol) and compound 4 (1.5 g, 5.0 mmol) in methanol (10 mL) was refluxed overnight under a nitrogen atmosphere. The reaction mixture was cooled to rt, filtered, and washed with methanol to afford 6 as a pinkish brown solid (1.26 g, 68%). ESI-MS m/e 372.1 (M+1).

Workup

  1. filtrationfiltered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-d0b38fb336074fa4b1866e2678be1cd1
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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