Sodium hydride → HCID 59570320, compound

HRID 1880702Notes

Reaction equation

HRID 1880702 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.Cl[CH2:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=1.[Cl-].[NH4+]>CN(C)C=O>[F:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[F:29])[C:22]([O:21][CH2:20][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:31]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59570369HCID 59570369, compoundHCID 178517507HCID 178517507, compound

Product 1

HCID 59570320HCID 59570320, compoundYield 17.3%

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 15 minutes, 0.21 g of chloromethyl-3,4-difluorobenzoate was added, and the mixture was stirred at 70° C. for 4 hours. 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 0.06 g of [3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]methyl 3,4-difluorobenzoate (present compound (42)).

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred at 70° C. for 4 hours
  3. extractionfollowed by extraction with ethyl acetate three times
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c08925d7cd744b3bc2a09d8b09a1357
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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