Water → HCID 11720261, compound

HRID 892252Notes

Reaction equation

HRID 892252 reaction equation
[N:1]1([CH2:6][CH2:7][S:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[O:9])[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[CH2:21][C:22]1[N:23]=[C:24]([CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[CH:31][CH:30]=2)[O:25][CH:26]=1.O>CN(C)C=O>[F:38][CH:36]([F:37])[O:35][C:32]1[CH:33]=[CH:34][C:29](/[CH:28]=[CH:27]/[C:24]2[O:25][CH:26]=[C:22]([CH2:21][O:17][C:14]3[CH:13]=[CH:12][C:11]([CH2:10][S:8]([CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[N:2]4)=[O:9])=[CH:16][CH:15]=3)[N:23]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 222420754-(2-[1,2,3]Triazol-1-yl-ethanesulfinylmethyl)-phenolHCID 691125744-(Chloromethyl)-2-{2-[4-(difluoromethoxy)phenyl]ethenyl}-1,3-oxazole

Product 1

HCID 11720261HCID 11720261, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 126 mg (0.50 mmol) 4-(2-[1,2,3]triazol-1-yl-ethanesulfinylmethyl)-phenol in 4 ml N,N-dimethylformamide was treated at 0° C. with 14 mg (0.55 mmol) sodium hydride and stirred at that temperature for 30 min, then 143 mg (0.50 mmol) 4-chloromethyl-2-[2-(4-difluoromethoxy-phenyl)-vinyl]-oxazole were added and stirring continued over night at room temperature. After addition of 8 ml water, the precipitate was isolated, washed thoroughly with water, and purified on silica. Elution with ethyl acetate/methanol (0 to 20%) yielded 123 mg (33%) 1-[2-(4-{2-[2-(E)-(4-difluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl-methanesulfinyl)-ethyl]-1H-[1,2,3]triazole as beige solid.

Workup

  1. stirringstirring
  2. waitcontinued over night at room temperature
  3. customthe precipitate was isolated
  4. washwashed thoroughly with water
  5. custompurified on silica
  6. washElution with ethyl acetate/methanol (0 to 20%)

Sources & evidence

ORD record
ord-6faa75fe6c90495bbb41a822ec023070
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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