Sodium Iodide → 3-(2-methyl-2-oxiranylmethyl)-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one
Reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13](=[O:15])[NH:12][N:11]=2)=[CH:6][CH:5]=1.C1(C)C=CC(S(O[CH2:28][C:29]2([CH3:32])[CH2:31][O:30]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[CH3:28][C:29]1([CH2:32][N:12]2[N:11]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:16])[F:17])=[CH:9][CH:8]=3)[O:14][C:13]2=[O:15])[CH2:31][O:30]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one (3.18 g, 12.92 mmol) prepared in Reference Example 49, (2-methyl-2-oxiranylmethyl) toluene-4-sulfonate (4.80 g, 19.38 mmol), potassium carbonate (2.14 g, 15.50 mmol) and sodium iodide (2.90 g, 19.38 mmol) in DMF (30 ml) was stirred at room temperature for 24 hours, and then at 60° C. for 4 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to afford 3-(2-methyl-2-oxiranylmethyl)-5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one (2.37 g, yield 58%) as a colorless crystalline powder.
Workup
- waitat 60° C. for 4 hours
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)
Sources & evidence
- ORD record
- ord-9c81ed7bbf2c4f78aa25aef3e1245424
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07262212B2
Reaction notes
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