Water → 1-[2-(2-Methyl-4-{2-[2-(e)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl-methanesulfinyl)-ethyl]-1h[1,2,3]triazole

HRID 892260Notes

Reaction equation

HRID 892260 reaction equation
C[C:2]1[CH:7]=[C:6]([CH2:8][S:9]([CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[O:10])[CH:5]=[CH:4][C:3]=1[OH:18].[H-].[Na+].Cl[CH2:22][C:23]1[N:24]=[C:25]([CH:28]=[CH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)[O:26][CH:27]=1.O.[CH3:42]N(C)C=O>>[CH3:42][C:7]1[CH:2]=[C:3]([O:18][CH2:22][C:23]2[N:24]=[C:25](/[CH:28]=[CH:29]/[C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)[O:26][CH:27]=2)[CH:4]=[CH:5][C:6]=1[CH2:8][S:9]([CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[N:14]1)=[O:10]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 222420732-Methyl-4-(2-[1,2,3]triazol-1-yl-ethanesulfinylmethyl)-phenolHCID 690715774-Chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole

Product 1

HCID 222420681-[2-(2-Methyl-4-{2-[2-(e)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl-methanesulfinyl)-ethyl]-1h[1,2,3]triazoleYield 24%

Procedure

A solution of 133 mg (0.50 mmol) 2-methyl-4-(2-[1,2,3]triazol-1-yl-ethanesulfinylmethyl)-phenol in 4 ml N,N-dimethylformamide was treated at 0° C. with 24 mg (0.60 mmol) 60% sodium hydride and stirred at that temperature for 30 min, then 152 mg (0.50 mmol) 4-chloromethyl-2-[2-(4-trifluoromethoxy-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, methanol/water 1:1, ether and purified by chromatography on silica. Gradient elution with ethyl acetate (5 to 10% methanol) gave 65 mg (24%) 1-[2-(2-methyl-4-{2-[2-(E)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl-methanesulfinyl)-ethyl]-1H-[1,2,3]triazole as solid.

Workup

  1. stirringstirring
  2. waitcontinued over night at room temperature
  3. customthe precipitate was isolated
  4. washwashed thoroughly with water, methanol/water 1:1, ether
  5. custompurified by chromatography on silica
  6. washGradient elution with ethyl acetate (5 to 10% methanol)

Sources & evidence

ORD record
ord-63802ce99bfc49d2bc55357e9b14b15e
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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