Nitroethane → tert-Butyl 6-cyano-2-pyridylmethylcarbamate

HRID 748170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748170
C[N+:2]([O-])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12]N=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C[Si](C#[N:22])(C)C.CN(C)C(Cl)=O.[N+:29]([CH2:32][CH3:33])([O-])=O>>[C:32]([C:33]1[N:22]=[C:15]([CH2:10][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH:14]=[CH:13][CH:12]=1)#[N:29]

Komponenten

5

Edukt 4

HCID 6587NitroethaneHCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86596460tert-butyl methyl(2-pyridyl)carbamate N-oxide

Produkt 1

HCID 22939432tert-Butyl 6-cyano-2-pyridylmethylcarbamateAusbeute 77 %

Versuchsvorschrift

A mixture of tert-butyl methyl(2-pyridyl)carbamate N-oxide (14.1 g, 63 mmol), trimethylsilyl cyanide (12.5 g, 126 mmol), N,N-dimethylcarbamoyl chloride (13.5 g, 125 mmol) and nitroethane (120 ml) was stirred at room temperature for 48 hrs. The reaction mixture was concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (10:1, v/v) and recrystallized from ethyl acetate-hexane to give the titled compound (11.3 g, 77%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washeluted with hexane-ethyl acetate (10:1
  3. customv/v) and recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-9dee629b34e845b99c756c47360cd8e1
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399759B2

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