Hydrochloric Acid → (2E)-2-[2-[(3-chlorophenoxy)methyl]phenyl]-2-methoxyimino-N-methylacetamide

HRID 1492038Notes

Reaction equation

HRID 1492038 reaction equation
CO[C:3](=[O:16])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14]Br)=[N:5]/[O:6][CH3:7].[Cl:17][C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][NH2:32].Cl>CN(C=O)C.CO>[CH3:31][NH:32][C:3](=[O:16])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([Cl:17])[CH:19]=1)=[N:5]/[O:6][CH3:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 10989774(E)-Methyl 2-(methoxyimino)-2-[2-(bromomethyl)phenyl]acetate

Product 1

HCID 22600150(2E)-2-[2-[(3-chlorophenoxy)methyl]phenyl]-2-methoxyimino-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl-(E)-2-(bromomethylphenyl)-2-methoxyiminoacetate as obtained in Example 27 (1) (250 mg), 3-chlorophenol (225 mg) and potassium carbonate (482 mg) were dissolved in DMF, and the resultant mixture was stirred at room temperature for 10 hours. A solution (677 mg) of methylamine in 30% methanol was added thereto, and stirring was continued for 10 hours. The reaction mixture was neutralized with dilute hydrochloric acid, extracted with diethyl ether. The solvent was dried and evaporated, and the residue was purified by silica gel column chromatography to give 265 mg of the objective compound.

Workup

  1. extractionextracted with diethyl ether
  2. customThe solvent was dried
  3. customevaporated
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-845c4510daf14c299226a573f9bf88fc
Source dataset
uspto-grants-1994_12
Patent number
US05371223

Reaction notes

Loading…