Isopropenyl chloroformate → (2RS)-1-(Isopropenyloxycarbonyl)-2-methyl-1,2-dihydro-1,4,6-triazanaphthalen-3(4H)-one

HRID 21530

Reaktionsgleichung

Reaktionsgleichung von HRID 21530
[CH3:1][CH:2]1[C:11](=[O:12])[NH:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[NH:3]1.Cl[C:14]([O:16][C:17]([CH3:19])=[CH2:18])=[O:15]>N1C=CC=CC=1>[C:17]([O:16][C:14]([N:3]1[C:4]2[C:9](=[CH:8][N:7]=[CH:6][CH:5]=2)[NH:10][C:11](=[O:12])[CH:2]1[CH3:1])=[O:15])([CH3:19])=[CH2:18]

Komponenten

4

Edukt 2

HCID 93846Isopropenyl chloroformateHCID 199328812-methyl-1H,2H,3H,4H-pyrido[3,4-b]pyrazin-3-one

Produkt 1

HCID 19932849(2RS)-1-(Isopropenyloxycarbonyl)-2-methyl-1,2-dihydro-1,4,6-triazanaphthalen-3(4H)-oneAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

(2RS)-2-Methyl-1,2-dihydro-1,4,6-triazanaphthalen-3(4H)-one (A. Albert, G. B. Barlin J. Chem. Soc. 1963, 5156) (570 mg, 3.5 mmol) was dissolved in 30 ml of anhydrous pyridine and cooled in an ice bath. 0.42 ml (3.8 mmol) of isopropenyl chloroformate was added dropwise, and the mixture was subsequently stirred at room temperature overnight. Concentration, chromatography on silica gel (ethyl acetate/methanol=20:1) and crystallization (pentane/diethyl ether) resulted in 100 mg (12%) of the desired product of melting point 170°-171° C.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. concentrationConcentration, chromatography
  3. customon silica gel (ethyl acetate/methanol=20:1) and crystallization (pentane/diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-51bf8dc81a7448649807c64ccbba7baf
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424311

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