Methyl iodide → N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-methyloxy-benzamide

HRID 275858Notes

Reaction equation

HRID 275858 reaction equation
[CH3:1][N:2]([O:23][CH3:24])[C:3](=[O:22])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].CI.[C:27](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][N:2]([O:23][CH3:24])[C:3](=[O:22])[C:4]1[CH:9]=[C:8]([O:10][CH3:27])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18315375N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide

Product 1

HCID 18315335N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-methyloxy-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An N,N-dimethylformamide (8 ml) solution of N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide (0.8 g), methyl iodide (0.2 g) and potassium carbonate (0.5 g) was stirred for 3 hours at 60° C. The reaction mixture was poured into ice-water, which was subjected to extraction with ethyl acetate. The organic layer was washed with water, which was dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give N-methyl-N-methyloxy 2-benzyloxycarbonylamino-5-methyloxy-benzamide as a yellow oily product (0.55 g).

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe organic layer was washed with water, which
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-de8aad5c85044e7793b17af50dc88e4f
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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