Sodium hydride → HCID 15376322, compound

HRID 2081633Notes

Reaction equation

HRID 2081633 reaction equation
[CH3:1][NH:2][C:3](=[O:16])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][OH:15])=[N:5]/[O:6][CH3:7].[H-].[Na+].Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1>C1COCC1.O>[CH3:1][NH:2][C:3](=[O:16])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1)=[N:5]/[O:6][CH3:7]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 15376320(E)-2-(2-Hydroxymethylphenyl)-2-methoxyimino-N-methyl-acetamide

Product 1

HCID 15376322HCID 15376322, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-N-methyl-2-(2-hydroxymethylphenyl)-2-methoxyiminoacetamide (0.10 g) in THF (10 ml), sodium hydride (60% oily suspension) (0.02 g) was added thereto, and the resultant mixture was stirred at room temperature for 10 minutes. To the reaction mixture, 2-chloro-5-trifluoromethylpyridine (0.10 g) was added, and stirring was continued at 60° C. for 1 hour. The reaction mixture was cooled, diluted with water, followed by extraction with dichloromethane. The solvent was dried over anhydrous sodium sulfate, and after removal of the solvent, purified by silica gel colum chromatography and recrystallized from n-hexane to give 0.11 g of the objective compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe solvent was dried over anhydrous sodium sulfate
  4. customafter removal of the solvent
  5. custompurified by silica gel colum chromatography
  6. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-66463203ce3f41478e5d0911dbf46773
Source dataset
uspto-grants-1993_02
Patent number
US05185342

Reaction notes

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