Water → methyl N-methoxy-N-propargylcarbamate

HRID 3402

Reaktionsgleichung

Reaktionsgleichung von HRID 3402
[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]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 12663380methyl N-methoxycarbamate

Produkt 1

HCID 18935021methyl N-methoxy-N-propargylcarbamateAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturewhile being cooled with ice
  2. temperatureThe mixture was heat-refluxed for 4 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

Quellen und Nachweise

ORD-Eintrag
ord-cf112f9f981e4357be02e4ddbd112b54
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733935

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