Sodium hydride → [3-(4-Trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]methyl 4-fluorobenzoate

HRID 1880698

Reaction equation

HRID 1880698 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.[F:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27]Cl)=[O:25])=[CH:22][CH:21]=1.[Cl-].[NH4+]>CN(C)C=O>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][N:15]2[C:14](=[O:16])[O:13][N:12]=[C:11]2[C:7]2[CH:6]=[C:5]([C:4]([F:3])([F:17])[F:18])[CH:10]=[CH:9][N:8]=2)=[O:25])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11401232Chloromethyl 4-fluorobenzoateHCID 178517507HCID 178517507, compound

Product 1

HCID 59570357[3-(4-Trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]methyl 4-fluorobenzoateYield 34.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 2 ml of N,N-dimethylformamide was suspended 0.07 g of sodium hydride (60% oily), and 0.3 g of 3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one was added at room temperature. After stirring for 15 minutes, 0.29 g of chloromethyl 4-fluorobenzoate 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 0.17 g of [3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]methyl 4-fluorobenzoate (present compound (38)).

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-2ae16a5139b847cba2266c2b81f198a7
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Linked notes

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