Water → N-methoxy-N-propargyl-p-chlorobenzamide

HRID 3404

Reaction equation

HRID 3404 reaction equation
[H-].[Na+].[CH3:3][O:4][NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[CH2:15](Br)[C:16]#[CH:17].O>O1CCCC1>[CH3:3][O:4][N:5]([CH2:17][C:16]#[CH:15])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 126105704-chloro-N-methoxybenzamide

Product 1

HCID 18935031N-methoxy-N-propargyl-p-chlorobenzamideYield 36.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.22 g of sodium hydride (60% in oil) was suspended in 10 ml of tetrahydrofuran, and 1.0 g of N-methoxy-p-chlorobenzamide and 0.68 g of propargyl bromide were added thereto in this order while being cooled with ice. The mixture was heat-refluxed for 8 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 0.44 g of N-methoxy-N-propargyl-p-chlorobenzamide.

Workup

  1. temperaturein this order while being cooled with ice
  2. temperatureThe mixture was heat-refluxed for 8 hours
  3. additionwas added to the reaction solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe extract was dried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-70e031461ff64ee8941f84d430c91d71
Source dataset
uspto-grants-1998_03
Patent number
US05733935

Linked notes

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