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Potassium Carbonate → 4-[4-(4-Fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzamidoxime

HRID 1387632
Notes
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Reaction equation

HRID 1387632 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Cl.[NH2:34][OH:35]>CCO.O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[N:13]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1](=[N:34][OH:35])[NH2:2])=[CH:8][CH:7]=3)[NH:10][C:11]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 154078722-(4-cyanophenyl)4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazole

Product 1

HCID 1361462794-[4-(4-Fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzamidoximeYield 92.4%

Reagents, catalysts & solvents 2

HCID 702Ethanol
Solvent
HCID 962WaterSolvent2×

Procedure

To a mixture of 2-(4-cyanophenyl)-4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazole (3.0 g, 8.7 mmol) [See Ex. 1 above] and K2CO3 (2.4 g, 17 mmol) in EtOH (120 mL) and H2O (6 mL) was added hydroxylamine hydrochloride (1.2 g, 17 mmol). After heating at reflux for 24 h, the reaction mixture was poured into H2O. The precipitate was collected, washed with H2O and air-dried. The crude product was dissolved in acetone, silica gel was added and the solvent was evaporated. The impregnated silica gel was added to the top of a flash column and the column was eluted with a solvent gradient of 2-10% MeOH/CHCl3 to afford the title compound as a white solid (3.0 g, 91%): ESMS (m/z): 374 (M++H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 24 h
  3. customThe precipitate was collected
  4. washwashed with H2O
  5. customair-dried
  6. dissolutionThe crude product was dissolved in acetone
  7. additionsilica gel was added
  8. customthe solvent was evaporated
  9. additionThe impregnated silica gel was added to the top of a flash column
  10. washthe column was eluted with a solvent gradient of 2-10% MeOH/CHCl3

Sources & evidence

ORD record
ord-d23537a6574349caba563d2a25b30924
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06268370B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes