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Water → 4-[N-(4-hydroxyphenylmethyl)-N-(1H-imidazol-1-yl)amino]benzonitrile

HRID 446166
Notes
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Reaction equation

HRID 446166 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[N:10]1([NH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH:14]=[CH:13][N:12]=[CH:11]1.C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:15]([C:16]2[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=2)[N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 41663BromocresolHCID 230181884-[(1H-imidazol-1-yl)amino]benzonitrile

Product 1

HCID 114831434-[N-(4-hydroxyphenylmethyl)-N-(1H-imidazol-1-yl)amino]benzonitrileYield 41%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

4-hydroxybenzylbromide (15.6 g, 84.3 mmol, prepared following Wissner A. et al., J. Med. Chem. 1992, 35, 1650) was added to a mixture of 4-[N-(1H-imidazol-1-yl)amino]benzonitrile (10.00 g, 54.30 mmol) and K2CO3 (8.20 g, 59.70 mmol) in dry THF (150 ml) at room temperature. The mixture was then stirred at room temperature for 2 h and after poured into water and extracted with ethyl acetate, dried over Na2SO4, filtered, and concentrated under vacuum to give the crude product (16.00 g as solid). Crystallization from ethyl acetate with ethanol yielded the expected product (6.50 g, 41%, mp: 180° C.)

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give the crude product (16.00 g as solid)
  6. customCrystallization from ethyl acetate with ethanol

Sources & evidence

ORD record
ord-e1422b50b48247d685f6ff4baf9a7656
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08476455B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes