Reaction #56860

Reaction equation

4-nitro-benzaldehyde

tosylmethyl isocyanide

potassium carbonate

→

5-(4-nitro-phenyl)-oxazole

Yield 89.0%

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 30 minutes
3. 3
   ConcentrationAfter concentrating under reduced pressure
4. 4
   FiltrationThe solid that was filtered

Procedure

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).

Source