Acetate → HCID 59570371, compound

HRID 1880679Notes

Reaction equation

HRID 1880679 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]([O-:22])(=[O:21])[CH3:20].[Cl-].[NH4+].[CH3:25]N(C)C=O>>[C:19]([O:22][CH2:25][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:21])[CH3:20]

Participants

6

Reactant 5

HCID 175AcetateHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178517507HCID 178517507, compound

Product 1

HCID 59570371HCID 59570371, compound

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, 0.14 g of chloromethyl=acetate was added, and the mixture was stirred for 2 hours, and at 60° C. for 3 hours. This mixture was allowed to cool to room temperature, and 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 0.13 g of 4-(acetoxy)methyl-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (Present compound (13)).

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred 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-f98b5def4b984c47a9f2dcd8b9c07dea
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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