Water → methyl N-methoxy-N-propargylcarbamate
Reaction equation
[H-].[Na+].[CH3:3][O:4][NH:5][C:6](=[O:9])[O:7][CH3:8].[CH2:10](Br)[C:11]#[CH:12].O>O1CCCC1>[CH3:3][O:4][N:5]([CH2:12][C:11]#[CH:10])[C:6](=[O:9])[O:7][CH3:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.43 g of sodium hydride (60% in oil) was suspended in 10 ml of tetrahydrofuran, and 1.0 g of methyl N-methoxycarbamate and 1.36 g of propargyl bromide were added to the suspension in this order while being cooled with ice. The mixture was heat-refluxed 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 0.8 g of methyl N-methoxy-N-propargylcarbamate.
Workup
- temperaturewhile being cooled with ice
- temperatureThe mixture was heat-refluxed for 4 hours
- additionwas added to the reaction solution
- extractionthe mixture was extracted with ethyl acetate
- customThe extract was dried
- concentrationconcentrated
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-cf112f9f981e4357be02e4ddbd112b54
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05733935
Reaction notes
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