Water → HCID 57075227, compound

HRID 581109Notes

Reaction equation

HRID 581109 reaction equation
[CH2:1]([O:8][N:9]=[CH:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[N:24][O:25][CH3:26])[C:20]([O:22]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][NH2:28].O>CO>[CH3:27][NH:28][C:20](=[O:22])[C:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][O:11][CH:10]=[N:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[N:24][O:25][CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 57067711HCID 57067711, compound

Product 1

HCID 57075227HCID 57075227, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 2-(2-benzyloxyiminomethyloxymethylphenyl)-2-methoxyiminoacetate) (compound No 2) (200 mg, 0.6 mmol) was dissolved into 8 ml of methanol, an aqueous solution of 40% methylamine (230 mg, 2.9 mmol) was added thereto. After stirring for 1 day, water was added to the reaction solution, methanol was removed by evaporation, and there was extracted with ethyl acetate. The organic layer was rinsed with water and dried. After removing the solvent by evaporation, the residue was purified with silica gel chromatography to obtain 0.18 g of N- methyl 2-(2-benzyloxyiminomethyloxymethylphenyl)-2-methoxyiminoacetamide (Compound No. 3; yield: 90%). The proton NMR spectrum of the compound is 2.81 s (3H); 3.89 s (3H); 4.91 s (2H); 5.00 s (2H); 6.52 s (1H); 6.82 bd (1H); 7.15-7.21 m (1H); 7.23-7.47 m (8H) (solvent: CDCl3).

Workup

  1. customwas removed by evaporation, and there
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was rinsed with water
  4. customdried
  5. customAfter removing the solvent
  6. customby evaporation
  7. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-f7281cc1a01a4154a3ab703d009af8b4
Source dataset
uspto-grants-1999_07
Patent number
US05919825

Reaction notes

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