Dimethyl Sulfate → HCID 11046997, compound

HRID 273930Notes

Reaction equation

HRID 273930 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[N:20]\[OH:21])/[C:16]([NH:18][CH3:19])=[O:17])=[CH:3][CH:2]=1.[C:28](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[C:1]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[N:20]\[O:21][CH3:28])/[C:16]([NH:18][CH3:19])=[O:17])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 21756619HCID 21756619, compound

Product 1

HCID 11046997HCID 11046997, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To (E)-2-[2-(biphenyl-4-yloxymethyl)phenyl]-2-hydroxyimino-N-methylacetamide(9.73 g, 0.027 mol), added were dry acetone (100 ml), potassium carbonate (11.20 g, 0.081 mol) and dimethylsulfate (6.81 g, 0.054 mol), and the reaction mixture was stirred overnight at room temperature. Then, undissolved materials were removed therefrom and the remaining mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give (E)-2-[2-(biphenyl-4-yloxymethyl)phenyl]-2-methoxyimino-N-methylacetamide (9.85 g; yield, 97.4%) as colorless crystals.

Workup

  1. customThen, undissolved materials were removed
  2. concentrationthe remaining mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-0b0ee0812f9b4fddbfd029074126611b
Source dataset
uspto-grants-1995_02
Patent number
US05387714

Reaction notes

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