Dimethylformamide → 1-[4-[4-[2-[(E)-2-(4-trifluoromethylphenyl)ethenyl]oxazol-4-yl]methoxyphenyl]butyl-1H-imidazol-2-yl]-1-ethanol

HRID 1610945Notes

Reaction equation

HRID 1610945 reaction equation
CN(C=[O:5])C.[H-].[Na+].O[CH2:9][CH2:10][C:11]1[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH:13]=[CH:14][N:15]=1.[F:27][C:28]([F:45])([F:44])[C:29]1[CH:34]=[CH:33][C:32](/[CH:35]=[CH:36]/[C:37]2[O:38][CH:39]=[C:40]([CH2:42]Cl)[N:41]=2)=[CH:31][CH:30]=1>O>[F:27][C:28]([F:45])([F:44])[C:29]1[CH:34]=[CH:33][C:32](/[CH:35]=[CH:36]/[C:37]2[O:38][CH:39]=[C:40]([CH2:42][O:26][C:23]3[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][CH2:17][CH2:16][N:12]4[CH:13]=[CH:14][N:15]=[C:11]4[CH:10]([OH:5])[CH3:9])=[CH:25][CH:24]=3)[N:41]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 98571264-(chloromethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazoleHCID 222593234-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenol

Product 1

HCID 865928071-[4-[4-[2-[(E)-2-(4-trifluoromethylphenyl)ethenyl]oxazol-4-yl]methoxyphenyl]butyl-1H-imidazol-2-yl]-1-ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon atmosphere, DMF (4 ml) was added to a mixture of 65% sodium hydride (40.6 mg) and 4-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenol (260 mg) at 0° C. The mixture was stirred at room temperature for 30 min. [2-[(E)-2-(4-Trifluoromethylphenyl)ethenyl]oxazol-4-yl]methyl chloride (316 mg) was added to the mixture at 0° C., and the mixture was stirred at room temperature for 15 hr. Water was added to the mixture to give crystals. The crystals were collected by filtration, washed with water and isopropyl ether and recrystallized from acetone-hexane to give the titled compound (393 mg) as pale yellow needle crystals.

Workup

  1. additionwas added to the mixture at 0° C.
  2. customto give crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with water and isopropyl ether
  5. customrecrystallized from acetone-hexane

Sources & evidence

ORD record
ord-88982c8d1d9e49d28bbbae88c18db9eb
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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