Triethylamine → Benzyl prop-2-yn-1-ylcarbamate

HRID 49565

Reaktionsgleichung

Reaktionsgleichung von HRID 49565
[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)CC)C.[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)(=O)C>[C:20]([NH:4][CH2:1][C:2]#[CH:3])([O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 239041Propargylamine

Produkt 1

HCID 11137906Benzyl prop-2-yn-1-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of propargylamine (20 g) and triethylamine (60.7 mL) in ethyl acetate (500 mL) was added benzyloxycarbonyl chloride (71.7 g) slowly while maintaining the reaction temperature between −5° C. and +5° C. The mixture was then stirred at room temperature overnight. The mixture was washed sequentially with 1.5 M HCl (200 mL), 5% NaHCO3 in water (200 mL), and saturated aqueous sodium chloride (100 mL). The solvent was switched to hexane while the desired product precipitated as colorless crystals (60.1 g).

Aufarbeitung

  1. temperaturewhile maintaining the reaction temperature between −5° C. and +5° C
  2. washThe mixture was washed sequentially with 1.5 M HCl (200 mL), 5% NaHCO3 in water (200 mL), and saturated aqueous sodium chloride (100 mL)
  3. customprecipitated as colorless crystals (60.1 g)

Quellen und Nachweise

ORD-Eintrag
ord-528fffcb5f3048898cfbab694e12c1e8
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706885B2

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