Hydrochloric Acid → (2E)-2-[2-[[5-chloro-3-(trifluoromethyl)-2-pyridinyl]oxymethyl]phenyl]-2-methoxyimino-N-methylacetamide

HRID 1637015Notes

Reaction equation

HRID 1637015 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[N:14][O:15][CH3:16])[C:10]([NH:12][CH3:13])=[O:11].[H-].[Na+].Cl[C:20]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:23]([Cl:30])=[CH:22][N:21]=1.Cl>C1COCC1>[Cl:30][C:23]1[CH:24]=[C:25]([C:26]([F:29])([F:27])[F:28])[C:20]([O:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2/[C:9](=[N:14]\[O:15][CH3:16])/[C:10]([NH:12][CH3:13])=[O:11])=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 110421442,5-dichloro-3-(trifluoromethyl)pyridineHCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Product 1

HCID 22016901(2E)-2-[2-[[5-chloro-3-(trifluoromethyl)-2-pyridinyl]oxymethyl]phenyl]-2-methoxyimino-N-methylacetamideYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide (300 mg) was dissolved in THF (5 ml). 60% Sodium hydride (65 mg) was added, and the mixture was stirred for 10 minutes. 2,5-Dichloro-3-trifluoromethylpyridine (350 mg) was added, and the mixture was stirred at room temperature for 12 hours, neutralized with 1N-hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to obtain the title compound (398 mg, yield: 74%).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4999b3b427434885b3e687af07bc5c74
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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