3,5-Dimethylpyrazole → HCID 23024917, compound

HRID 349935Notes

Reaction equation

HRID 349935 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.O1CCCC1.Cl[CH2:16][C:17]1[CH:36]=[CH:35][C:20]([O:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:19][CH:18]=1>O>[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])=[CH:35][CH:36]=2)[N:5]=1

Participants

6

Reactant 4

HCID 62103,5-DimethylpyrazoleHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Product 1

HCID 23024917HCID 23024917, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60%, oily, 880 mg) was added to a mixture of 3,5-dimethylpyrazole (2.11 g) and tetrahydrofuran (50 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. After 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (6.28 g) was added to the reaction mixture, the mixture was refluxed for 24 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and 3,5-dimethyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole (5.49 g, yield: 74%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 86–87° C.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3b508f66d7e34a2c8ca766babaae667d
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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