Sodium hydride → HCID 59570325, compound

HRID 1880674Notes

Reaction equation

HRID 1880674 reaction equation
[H-].[Na+].[F:3][C:4]([F:18])([F:17])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:12][O:13][C:14](=[O:16])[N:15]=2)[CH:6]=1.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21].[Cl-].[NH4+]>CN(C)C=O>[CH3:21][C:20]([CH3:23])([CH3:22])[C:19]([N:15]1[C:14](=[O:16])[O:13][N:12]=[C:11]1[C:7]1[CH:6]=[C:5]([C:4]([F:3])([F:17])[F:18])[CH:10]=[CH:9][N:8]=1)=[O:24]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 178517507HCID 178517507, compound

Product 1

HCID 59570325HCID 59570325, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 2 ml of N,N-dimethylformamide was suspended 0.05 g of sodium hydride (60% oily), and 0.2 g of 3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one was added at room temperature. After stirring for 10 minutes, 0.12 g of pivaloyl chloride was added at 0° C., the mixture was stirred at room temperature for 2 hours, and at 60° C. for 3 hours, and the reaction solution was allowed to cool to room temperature, and poured into an aqueous saturated ammonium chloride solution, followed by extraction with ethyl acetate three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.16 g of 4-(2,2-dimethylpropionyl)-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (8)).

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. waitat 60° C. for 3 hours
  4. extractionfollowed by extraction with ethyl acetate three times
  5. washwashed with an aqueous saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-49cc690b392c472e8f7bf52f18a01202
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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