Thionyl Chloride → (2E)-2-[2-(chloromethyl)phenyl]-2-methoxyimino-N-methylacetamide

HRID 1637012Notes

Reaction equation

HRID 1637012 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[N:18][O:19][CH3:20])[C:14]([NH:16][CH3:17])=[O:15]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:3][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[C:13](=[N:18]\[O:19][CH3:20])/[C:14]([NH:16][CH3:17])=[O:15]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Product 1

HCID 15335384(2E)-2-[2-(chloromethyl)phenyl]-2-methoxyimino-N-methylacetamideYield 80%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

Thionyl chloride (3.0 ml) was added to a mixture of 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide (3.0 g), tetrabutylammonium chloride (380 mg) and toluene (30 ml) at room temperature. The mixture was stirred for 10 minutes, and then stirred at 60° C. for 1.5 hours. After the mixture was cooled by allowing it to stand, the solvent was evaporated under reduced pressure. The residue was dissolved in diethyl ether, and washed successively with water and saturated brine. The ether layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in a small amount of diethyl ether. Hexane was added to the solution to obtain the title compound as crystals (2.6 g, 80%).

Workup

  1. stirringstirred at 60° C. for 1.5 hours
  2. temperatureAfter the mixture was cooled
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washwashed successively with water and saturated brine
  6. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. dissolutionthe resulting residue was dissolved in a small amount of diethyl ether
  9. additionHexane was added to the solution

Sources & evidence

ORD record
ord-12f82a19d7aa44b6ac44c579dc5a42e4
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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