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

HRID 501537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501537
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].[C:14](OCC)(OCC)(OCC)[CH3:15].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH3:14][C:15]1[O:13][C:3]2[C:4]([C:5]#[N:6])=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=2[N:1]=1

Komponenten

5

Edukt 3

HCID 66221Triethyl orthoacetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 218754622-Amino-4-cyano-3-hydroxynitrobenzene

Produkt 1

HCID 218752867-Cyano-2-methyl-4-nitrobenzoxazoleAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

To a solution of 11A (0.2 g, 1.12 mmol) in xylene (6 mL) was added triethyl orthoacetate (0.62 mL, 3.35 mmol) and pyridinium p-toluenesulfonate (0.04 g, 1.12 mmol). The mixture was refluxed for 3 h, then allowed to cool to rt and partitioned between H2O and EtOAc. The separated EtOAc layer was concentrated under reduced pressure and the residue was chromatographed eluting with 20% EtOAc in hexane to afford compound 11B (0.16 g) as a solid.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h
  2. custompartitioned between H2O and EtOAc
  3. concentrationThe separated EtOAc layer was concentrated under reduced pressure
  4. customthe residue was chromatographed
  5. washeluting with 20% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-5be70b5d4cdb47a2a587418cdca47843
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772267B2

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