Diethyl Ether → HCID 59570380, compound

HRID 1880673Notes

Reaction equation

HRID 1880673 reaction equation
CN(C)C=O.[H-].[Na+].[F:8][C:9]([F:23])([F:22])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[NH:17][O:18][C:19](=[O:21])[N:20]=2)[CH:11]=1.[Cl-].[NH4+].[CH3:26][CH2:27][O:28][CH2:29]C>>[CH2:27]([O:28][CH2:29][N:20]1[C:19](=[O:21])[O:18][N:17]=[C:16]1[C:12]1[CH:11]=[C:10]([C:9]([F:8])([F:22])[F:23])[CH:15]=[CH:14][N:13]=1)[CH3:26]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178517507HCID 178517507, compound

Product 1

HCID 59570380HCID 59570380, 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, 0.12 g. of chloromethyl=ethyl=ether was added at 0° C., the mixture was stirred 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 tert-butyl=methyl=ether 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 0.21 g of 4-ethoxymethyl-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (7)).

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred at 60° C. for 3 hours
  3. extractionfollowed by extraction with tert-butyl=methyl=ether 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-5a02a599e55b460fb2fc938368918a07
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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