Triethyl orthoacetate → 7-Cyano-2-methyl-4-nitrobenzoxazole

HRID 723692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723692
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([C:9]#[N:10])[CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14](OCC)(OCC)(OCC)[CH3:15]>>[C:9]([C:6]1[C:7]2[O:8][C:14]([CH3:15])=[N:1][C:2]=2[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][CH:5]=1)#[N:10]

Komponenten

3

Edukt 2

HCID 66221Triethyl orthoacetateHCID 218754622-Amino-4-cyano-3-hydroxynitrobenzene

Produkt 1

HCID 218752867-Cyano-2-methyl-4-nitrobenzoxazoleAusbeute 63 %

Versuchsvorschrift

Compound 477B (0.360 g, 2.01 mmol) and triethyl orthoacetate (1.30 g, 8.04 mmol) were combined and heated at reflux under nitrogen for 1 h. The solvent was removed in vacuo and the resulting residue purified by flash chromatography eluting with 5% ether/CH2Cl2 to give 0.255 g (63%) of compound 477C as a brown solid. HPLC: 98.4% at 1.80 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10–90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 204.28 [M+H]+.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 1 h
  3. customThe solvent was removed in vacuo
  4. customthe resulting residue purified by flash chromatography
  5. washeluting with 5% ether/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-b2896d99cd384646bc45221828033be6
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141578B2

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