Sodium hydride → 1-(4-Chloro-6-methyl-2-pyridinyl)ethanone O-[(2,6-Dimethoxyphenyl)methyl] Oxime

HRID 1357033

Reaction equation

HRID 1357033 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9](=[N:11][OH:12])[CH3:10])[CH:3]=1.[H-].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:18]=1[CH2:19]Cl>CN(C)C=O>[CH3:26][O:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:17]([O:16][CH3:15])[C:18]=1[CH2:19][O:12][N:11]=[C:9]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127070022-(chloromethyl)-1,3-dimethoxyBenzeneHCID 1363883511-(4-Chloro-6-methyl-2-pyridinyl)ethanone oxime

Product 1

HCID 731784321-(4-Chloro-6-methyl-2-pyridinyl)ethanone O-[(2,6-Dimethoxyphenyl)methyl] Oxime

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

On the other hand, 1.66 g (9.0 mmol) of 1-(4-chloro-6-methyl-2-pyridinyl)ethanone oxime was dissolved in 15 ml of N,N-dimethylformamide, and the resultant solution was added with 0.18 g (4.39 mmol) of sodium hydride (60%, oiliness) while cooling the solution with ice. The mixture was stirred for 15 min. at a temperature below 0° C. and was added with the whole amount of the crude product of 2,6-dimethoxybenzyl chloride prepared previously while cooling the mixture with ice. The resultant mixture was stirred for 2.3 hours at a room temperature to complete a reaction. The reacted mixture was then poured into ice water. At that time, the target compound was precipitated in the ice water. The precipitation was taken out by filtering, washed with hexane and dried to thereby obtain the target compound in an amount of 2.3 g.

Workup

  1. temperaturewhile cooling the solution with ice
  2. customprepared previously
  3. temperaturewhile cooling the mixture with ice
  4. customa reaction
  5. customAt that time, the target compound was precipitated in the ice water
  6. customThe precipitation
  7. filtrationby filtering
  8. washwashed with hexane
  9. customdried
  10. customto thereby obtain the target compound in an amount of 2.3 g

Sources & evidence

ORD record
ord-55117f21121146beabd2e6f74c49a34b
Source dataset
uspto-grants-2003_07
Patent number
US06589967B1

Linked notes

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