Hydrogen Peroxide → 4-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine 1-oxide
Reaction equation
[OH:1]O.[CH2:3]([C:5]1[S:6][C:7]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=1)[CH3:4]>ClCCl.C[Re](=O)(=O)=O>[CH2:3]([C:5]1[S:6][C:7]([C:17]2[CH:22]=[CH:21][N+:20]([O-:1])=[CH:19][CH:18]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[N:9]=1)[CH3:4]Participants
Procedure
3.9 ml (44 mmol) of a 30% strength hydrogen peroxide solution are added dropwise with cooling to a solution of 2.18 g (7.24 mmol) of 4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine and 46.2 mg (0.19 mmol) of methyltrioxorhenium (VII) in 10 ml dichloromethane such that the temperature of the reaction mixture does not exceed 15° C., and the mixture is stirred at room temperature for 16 h. The reaction mixture is then diluted with 100 ml of dichloromethane, and the organic phase is washed successively with 30 ml of a saturated aqueous NaHCO3 solution, 30 ml of a saturated Na2SO3 solution and 30 ml of water and dried over MgSO4. Under reduced pressure, the product is freed from the solvent, giving 1.98 g (85%) of the desired product; 1H-NMR(DMSO-d6) δ: 8.12 (d, 2H), 7.53 (m, 2H), 7.25 (d, 2H), 7.21 (m, 2H), 3.03 (q, 2H), 1.36 (t, 3H).
Workup
- customdoes not exceed 15° C.
- washthe organic phase is washed successively with 30 ml of a saturated aqueous NaHCO3 solution, 30 ml of a saturated Na2SO3 solution and 30 ml of water
- dry with materialdried over MgSO4
Sources & evidence
- ORD record
- ord-0c546883ac6a4eeb9386a2bcfbc1e624
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09198426B2
Reaction notes
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