Phosphorus oxide (P4O10) → 2-(4-Bromophenyl)oxazole
Reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][CH:10]([O:14]CC)OCC)=O)=[CH:4][CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[O:14][CH:10]=[CH:9][N:8]=2)=[CH:17][CH:18]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
4-Bromo-N-(2,2-diethoxyethyl)benzamide was dissolved in concentrated sulfuric acid at 0° C. To phosphorus pentoxide (5.2 g, 18.3 mmol) was added the sulfuric acid solution, and the mixture was heated at 180° C. for 30 minutes. The reaction mixture was cooled down to room temperature, and poured into ice. The whole was made basic by addition of NaHCO3 and amnmonia aqueous solution. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give title compound (1.23 g, 70% yield).
Workup
- temperatureThe reaction mixture was cooled down to room temperature
- additionpoured into ice
- extractionThe whole was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1108a20530ce465f8a7471db52e3732f
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727238B2
Reaction notes
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