Water → HCID 17862359, compound

HRID 644919Notes

Reaction equation

HRID 644919 reaction equation
[CH3:1][O:2][CH2:3]Cl.[H-].[Na+].[CH3:7][NH:8][C:9]([N:11]1[C:15]([CH3:16])=[CH:14][C:13]([O:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:20][N:19]=2)=[N:12]1)=[O:10].O>CN(C=O)C>[CH3:7][N:8]([CH2:3][O:2][CH3:1])[C:9]([N:11]1[C:15]([CH3:16])=[CH:14][C:13]([O:17][C:18]2[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:27])([F:28])[F:26])=[CH:20][N:19]=2)=[N:12]1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 17862376HCID 17862376, compound

Product 1

HCID 17862359HCID 17862359, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloromethyl methyl ether (0.16 g, 2.0 mmol) was added to a solution of sodium hydride (60% in oil, 0.09 g, 2.2 mmol) and N-methyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (0.67 g, 2.0 mmol) in DMF (10 ml) at 0° C., and while the mixture was allowed to have room temperature gradually, the mixture was stirred overnight. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant. The solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/5), to give a colorless viscous substance of N-methyl-N-methoxymethyl-3-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-5-methylpyrazole-1-carboxamide (0.18 g, yield: 23.8%). 1H-NMR (CDCl3, TMS, ppm): δ 1.87 (s, 3H), 3.52 (s, 3H), 3.53 (s, 3H), 5.18 (s, 2H), 5.46 (s, 1H), 7.80-7.95 (m, 1H), 8.50-8.65 (m, 1H).

Workup

  1. customto have room temperature
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate (10 ml×3)
  4. washAn organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove a desiccant
  8. distillationThe solvent was distilled off from the filtrate under reduced pressure
  9. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-e836655834b6492f8493d62cc218c51c
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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