Methyl iodide → HCID 73197959, compound

HRID 1596148Notes

Reaction equation

HRID 1596148 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[CH3:9][O:10][N:11]=[C:12]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:29]([OH:34])[C:30](=[O:33])[O:31][CH3:32])=[CH:20][C:15]=2[O:14][CH2:13]1>CN(C)C=O.C(OCC)C>[CH3:9][O:10][N:11]=[C:12]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:29]([O:34][CH3:3])[C:30](=[O:33])[O:31][CH3:32])=[CH:20][C:15]=2[O:14][CH2:13]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 73886750HCID 73886750, compound

Product 1

HCID 73197959HCID 73197959, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

1.1 g of methyl iodide and 0.88 g of anhydrous potassium carbonate were added to a solution of 1.9 g of methyl N-[2-(3-methoxyimino-2,3-dihydro-benzofuran-6-yloxymethyl)phenyl]-N-hydroxycarbamate in 20 ml of N,N-dimethylformamide, and they were stirred at room temperature for 24 hours. The reaction solution was diluted with 200 ml of diethyl ether, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate) to obtain 1.5 g of the title compound (having a m. p. of 102-103° C. and 1H-NMR data shown in the following table].

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-0b5d383c560545c7ae980c7b944ffe2f
Source dataset
uspto-grants-2001_09
Patent number
US06291399B1

Reaction notes

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