Sodium hydride → HCID 15376322, compound

HRID 1491984Notes

Reaction equation

HRID 1491984 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 column 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 column chromatography
  6. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-64e7f12c98cf4a13863e93e5fda46d05
Source dataset
uspto-grants-1994_12
Patent number
US05371222

Reaction notes

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