4-Nitrobenzaldehyde → 2-(4-Nitrophenyl)oxazole
Reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O[CH:15](OCC)[CH2:16][NH2:17])C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[NH4+]>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[O:9][CH:15]=[CH:16][N:17]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of p-nitro benzaldehyde (3 g, 19.8 mmol) and 2,2-diethoxy-ethylamine (2.64 g, 19.8 mmol) was heated at 100° C. for 2 hrs. The reaction mixture was cooled to room temperature and sulphuric acid (20 ml) was added. The resultant solution was added slowly to a mixture of phosphorus pentoxide (10 g) and sulphuric acid (3 ml) at 180° C. and the temperature was maintained for 30 min. The reaction mixture was cooled to room temperature and basified with saturated ammonium hydroxide solution. The resultant solid was filtered and recrystallised with ether to give 2-(4-nitro-phenyl)-oxazole (1 g, 26%).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- temperaturethe temperature was maintained for 30 min
- filtrationThe resultant solid was filtered
- customrecrystallised with ether
Sources & evidence
- ORD record
- ord-ef213a016b824419965d14640f2689a7
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486962B2
Reaction notes
Loading…