Water → HCID 22259290, compound

HRID 1610954Notes

Reaction equation

HRID 1610954 reaction equation
[H-].[Na+].[F:3][C:4]([F:39])([F:38])[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[O:14][CH:15]=[C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][N:30]4[CH:34]=[CH:33][N:32]=[C:31]4[CH2:35][CH2:36][OH:37])=[CH:22][CH:21]=3)[N:17]=2)=[CH:7][CH:6]=1.[CH:40]([N:43]=[C:44]=[O:45])([CH3:42])[CH3:41].O>ClCCl>[CH:40]([NH:43][C:44](=[O:45])[O:37][CH2:36][CH2:35][C:31]1[N:30]([CH2:29][CH2:28][CH2:27][CH2:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][CH2:18][C:16]3[N:17]=[C:13](/[CH:12]=[CH:11]/[C:8]4[CH:9]=[CH:10][C:5]([C:4]([F:38])([F:3])[F:39])=[CH:6][CH:7]=4)[O:14][CH:15]=3)=[CH:21][CH:22]=2)[CH:34]=[CH:33][N:32]=1)([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 61277Isopropyl isocyanateHCID 22259324HCID 22259324, compound

Product 1

HCID 22259290HCID 22259290, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

65% Sodium hydride (21.6 mg) was added to a solution of 2-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]-1-ethanol (300 mg) in dichloromethane (3 ml) at 0° C., and the mixture was stirred at room temperature for 30 min. Isopropyl isocyanate (0.288 ml) was added to the mixture at 0° C., and the mixture was stirred at room temperature for 5 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was successively washed with 1N aqueous sodium hydroxide solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and recrystallized from ethyl acetate-hexane to give the titled compound (315 mg) as a colorless crystal powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was successively washed with 1N aqueous sodium hydroxide solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-50e9274290ea46e0a852bd0c22a30033
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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