Bromine → Ethyl 5-{4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl}-1,3,4-oxadiazole-2-carboxylate
Reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]=[N:6][NH:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])[CH2:12][CH2:11]1)=[O:9])[CH3:2].C([O-])(=O)C.[Na+].BrBr>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:5]1[O:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:25])([F:24])[F:26])[CH2:12][CH2:11]2)=[N:7][N:6]=1)=[O:28])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of {[4-(2-trifluoromethylbenzoyl)piperazine-1-carbonyl]-hydrazono}acetic acid ethyl ester (1.32 g, 3.29 mmol) and sodium acetate (1.01 g, 12.31 mmol) in acetic acid (5 mL) was added a solution of bromine (0.480 g, 3 mmol) in acetic acid (2 mL) at 0° C. The mixture was stirred for 1 hour at 0° C. and another hour at room temperature and then refluxed for 30 minutes. The solvents were removed in vacuo. The residue was diluted with water, extracted with dichloromethane. The organic layer was washed with water and then concentrated to yield the crude product. The title compound was obtained as a white solid in 49% yield (0.550 g) after purification by flash column chromatography.
Workup
- temperaturerefluxed for 30 minutes
- customThe solvents were removed in vacuo
- additionThe residue was diluted with water
- extractionextracted with dichloromethane
- washThe organic layer was washed with water
- concentrationconcentrated
- customto yield the crude product
Sources & evidence
- ORD record
- ord-53598292979f4f1fa3ad8a19bd30c064
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919496B2
Reaction notes
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