m-Chloroperbenzoic acid → 5-(Oxiran-2-yl)-2,1,3-benzoxadiazole
Reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]2=[N:7][O:8][N:9]=[C:5]2[CH:4]=1)=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[O:20]1[CH2:2][CH:1]1[C:3]1[CH:11]=[CH:10][C:6]2=[N:7][O:8][N:9]=[C:5]2[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-ethenyl-2,1,3-benzoxadiazole (1.80 g, 12.3 mmol) in DCM (20 mL) was slowly added m-CPBA (3.8 g, 22 mmol) at 0° C. The flask was warmed to room temperature; the mixture was then stirred for 12 hours. TLC as well as LC indicated that reaction had gone to completion. The mixture was washed with aqueous Na2S2O3, NaHCO3, and water. The organic layers was washed with brine and then concentrated. The residue was purified over silica gel to afford the title compound.
Workup
- customat 0° C
- customTLC as well as LC indicated that reaction
- washThe mixture was washed with aqueous Na2S2O3, NaHCO3, and water
- washThe organic layers was washed with brine
- concentrationconcentrated
- customThe residue was purified over silica gel
Sources & evidence
- ORD record
- ord-9b1e90322f5a456fb9af78d4c1cf850a
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206199B2
Reaction notes
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