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Acetic Acid → 4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzonitrile

HRID 1051168
Notes
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Reaction equation

HRID 1051168 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:33](=O)[CH:34]([CH3:36])[CH3:35].C(O)(=O)C>ClCCl>[CH3:33][CH:34]([CH3:36])[CH2:35][NH:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 683868484-(4-amino-1H-benzimidazol-1-yl)benzonitrile

Product 1

HCID 683865174-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzonitrileYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred solution of 4-(4-amino-1H-benzimidazol-1-yl)benzonitrile (246 mg, 1.05 mmol) in dichloromethane (10 mL) at rt was added sodium triacetoxy borohydride (311 mg, 1.47 mmol, 1.4 eq), isobutyraldehyde (91 mg, 1.26 mmol, 1.2 eq) and acetic acid (63 m g, 1.05 mmol, 1 eq) and the mixture was stirred for 2 h. The mixture was poured on water and extracted with DCM. After evaporation of the organic phase, purification of the residue by flash chromatography yielded 190 mg 4-{4-[(2-methylpropyl)amino]-1H-benzimidazol-1-yl}benzonitrile (62.3%).

Workup

  1. additionThe mixture was poured on water
  2. extractionextracted with DCM
  3. customAfter evaporation of the organic phase, purification of the residue by flash chromatography

Sources & evidence

ORD record
ord-14149e3fd1da4d5a8482be05af6d9a95
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09388140B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes