Sodium hydride → HCID 59570303, compound

HRID 1880670Notes

Reaction equation

HRID 1880670 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.[CH:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1.[Cl-].[NH4+]>CN(C)C=O>[CH:19]1([C:22]([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:23])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 178517507HCID 178517507, compound

Product 1

HCID 59570303HCID 59570303, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 2 ml of N,N-dimethylformamide was suspended 0.04 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 0° C. After stirring for 10 minutes, 0.12 g of cyclopropanecarbonyl chloride was added, and the mixture was stirred at 50° C. for 4 hours. Thereafter, the reaction solution was 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 0.08 g of 4-cyclopropanecarbonyl-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (4)).

Workup

  1. additionwas added at 0° C
  2. stirringthe mixture was stirred at 50° 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-b3b74e0ee86b4a55a3e85d43f6f810e3
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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