4-Nitrobenzaldehyde → 5-(4-Nitrophenyl)-1,3-oxazole

HRID 28582

Reaktionsgleichung

Reaktionsgleichung von HRID 28582
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].S([CH2:22][N+:23]#[C-:24])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[O:9][CH:24]=[N:23][CH:22]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 5414-NitrobenzaldehydeHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanide

Produkt 1

HCID 27370685-(4-Nitrophenyl)-1,3-oxazoleAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-nitro-benzaldehyde (5.0 g, 33.1 mmol), tosylmethyl isocyanide (6.4 g, 33.1 mmol) and potassium carbonate (7.8 g, 82.7 mmol) in methanol (100 ml) was heated under reflux for 30 minutes. After concentrating under reduced pressure, the residue was stirred with water (50 ml). The solid that was filtered to afford 5-(4-nitro-phenyl)-oxazole (5.6 g, 89% yield). 1H NMR (acetone-d6) δ 7.89 (s, 1H, Ar), 8.05 (d, 2H, J=9.3 Hz, Ar), 8.35-8.38 (m, 3H, Ar).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationAfter concentrating under reduced pressure
  4. filtrationThe solid that was filtered

Quellen und Nachweise

ORD-Eintrag
ord-bc34d81bc3ce4fa792e5254ed320c347
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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