Methyl iodide → HCID 59570342, compound

HRID 1880669Notes

Reaction equation

HRID 1880669 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.I[CH3:20].[Cl-].[NH4+]>CN(C)C=O.O1CCCC1>[CH3:20][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

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178517507HCID 178517507, compound

Product 1

HCID 59570342HCID 59570342, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into 3 ml of tetrahydrofuran was suspended 0.06 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 0° C. The mixture was stirred at room temperature for 10 minutes, 0.22 g of iodomethane and 1 ml of dimethylformamide were added, and the mixture was stirred at 40° C. for 3 hours. Thereafter, the reaction solution was 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 0.26 g of 4-methyl-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (3)).

Workup

  1. additionwas added at 0° C
  2. stirringthe mixture was stirred at 40° 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-347e79e260ab4894b78f05fd36cfef9a
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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