Water → N-methoxy-N-propargyloxymethylbenzamide

HRID 3406Notes

Reaction equation

HRID 3406 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][O:20][CH2:21][C:22]#[CH:23].O>C(#N)C>[CH3:1][O:2][N:3]([CH2:19][O:20][CH2:21][C:22]#[CH:23])[C:4](=[O:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 122413411-Propyne, 3-(chloromethoxy)-HCID 12355457N-Methoxybenzamide

Product 1

HCID 18935030N-methoxy-N-propargyloxymethylbenzamideYield 91.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.6 g of N-methoxybenzamide was dissolved in 10 ml of acetonitrile, and 0.55 g of potassium carbonate and 0.42 g of chloromethylpropargyl ether were added thereto in this order. The mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried, concentrated and purified by silica gel column chromatography to obtain 0.8 g of N-methoxy-N-propargyloxymethylbenzamide.

Workup

  1. additionwas added to the reaction solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-78a2d25f14b9434b93e8ef7743620d47
Source dataset
uspto-grants-1998_03
Patent number
US05733935

Reaction notes

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