Water → N-methoxy-N-propargyloxymethylbenzenesulfonamide

HRID 3407Notes

Reaction equation

HRID 3407 reaction equation
[CH3:1][O:2][NH:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][O:21][CH2:22][C:23]#[CH:24].O>C(#N)C>[CH3:1][O:2][N:3]([CH2:20][O:21][CH2:22][C:23]#[CH:24])[S:4]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)(=[O:6])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 270783N-MethoxybenzenesulfonamideHCID 122413411-Propyne, 3-(chloromethoxy)-

Product 1

HCID 18935034N-methoxy-N-propargyloxymethylbenzenesulfonamideYield 85.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.6 g of N-methoxybenzenesulfonamide was dissolved in 10 ml of acetonitrile, and 0.44 g of potassium carbonate and 0.34 g of chloromethylpropargyl ether were added thereto in this order. The mixture was stirred at room temperature for 4 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 0.7 g of N-methoxy-N-propargyloxymethylbenzenesulfonamide.

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-8a7f1a41a70a4d3db418869aba312fea
Source dataset
uspto-grants-1998_03
Patent number
US05733935

Reaction notes

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