Diethyl Sulfate → 1-acetamido-N-ethyl phenazine

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Reaktionsgleichung

[C:1]([NH:4][C:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].S(OCC)(O[CH2:23][CH3:24])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[C:1]([NH:4][C:5]1[C:18]2[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:23][CH3:24])[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

Edukt 3

HCID 6163Diethyl Sulfate

HCID 11430Potassium Carbonate

HCID 57896198N-(Phenazin-1-yl)acetamide

Produkt 1

HCID 673514621-acetamido-N-ethyl phenazine

Versuchsvorschrift

Scheme 8 provides a synthetic route to a 1-acetamido-N-ethyl phenazine derivative (35). A 3-amino-catechol hydrochloride (30) is reacted with silver oxide and anhydrous sodium sulfate in ethyl acetate to give 3-amino-1,2-quinone (31), which is further reacted in situ with ortho phenylenediamine (32) to give 1-amino phenazine (33). The amino phenazine (33) is acetylated with acetic anhydride in acetic acid to give 1-acetamido phenazine (34). The resulting 1-acetamido phenazine is reacted with diethyl sulfate in the presence of potassium carbonate to give N-ethyl-1-acetamido-phenazine (35)

Quellen und Nachweise

ORD-Eintrag: ord-a92b3aa369e947419488bffbcf3591cb
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08008037B2

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