Pyrazole → HCID 21478980, compound

HRID 2292657Notes

Reaction equation

HRID 2292657 reaction equation
CN(C)C=O.[H-].[Na+].[NH:8]1[CH:12]=[CH:11][CH:10]=N1.[N:13]1([CH2:18][C:19]2[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH2:25][CH2:26][NH-:27])=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[N:14]1>C(OCC)(=O)C>[N:13]1([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:23][CH2:24][CH2:25][CH2:26][N:27]3[CH:10]=[CH:11][CH:12]=[N:8]3)=[CH:28][CH:29]=2)[CH:17]=[CH:16][CH:15]=[N:14]1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 86751497HCID 86751497, compound

Product 1

HCID 21478980HCID 21478980, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of anhydrous N,N-dimethylformamide (5 ml) and sodium hydride (60% oil dispersion) (62 mg) was added pyrazole (100 mg), and the mixture was stirred for 30 minutes. An anhydrous N,N-dimethylformamide solution (5 ml) of 3-[4-(1-pyrazolyl)methylphenoxy]propylamide (produced in Reference Production Example 1 described below) (434 mg) was then added dropwise, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was then diluted with ethyl acetate (50 ml), which was washed twice with saturated aqueous ammonium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting oil was subjected to silica gel column chromatography, which afforded 340 mg of 1-{3-[4-(1-pyrazolyl)methylphenoxy]propyl}pyrazole (compound 31) in colorless oil. Yield, 82%.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. washwas washed twice with saturated aqueous ammonium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5994f2ba3b8495eb536b6260dd35aa5
Source dataset
uspto-grants-1997_11
Patent number
US05684022

Reaction notes

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