Diethyl Ether → 3-Chloro-2-(4-chloro-2-fluorophenyl)-2,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole-5-oxide
Reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[F:25])[N:16]=[C:15]2[CH2:26][CH2:27][S:28][CH2:29][C:14]=12.CCOCC.CCCCC>C(Cl)(Cl)Cl>[Cl:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[F:25])[N:16]=[C:15]2[CH2:26][CH2:27][S:28](=[O:9])[CH2:29][C:14]=12Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1.6 parts of 85% m-chloroperbenzoic acid dissolved in 110 parts of chloroform were added dropwise for 1 hour to a stirred solution of 3-chloro-2-(4-chloro-2-fluorophenyl)-2,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole dissolved in 75 parts of chloroform. The resulting solution was stirred 16 hours, washed 4 times with 40 parts of saturated aqueous NaHCO3, 2 times with water, dried with anhydrous magnesium sulfate, and solvent evaporated under a reduced pressure of 50 to 300 mm Hg. to give a pale yellow oil. The oil, when contacted with a mixture of ether and pentane, gave 1.2 parts of 3-chloro-2-(4-chloro-2-fluorophenyl)-2,4,6,7-tetrahydro-thiopyrano[4,3-c]pyrazole-5-oxide as a pale caramel-colored solid, m.p. 119°-122° C. This solid can be recrystallized from a mixture of methylene chloride, ether, and pentane to give m.p. 1221/2°-125° C.
Workup
- washwashed 4 times with 40 parts of saturated aqueous NaHCO3, 2 times with water
- dry with materialdried with anhydrous magnesium sulfate, and solvent
- customevaporated under a reduced pressure of 50 to 300 mm Hg
- customto give a pale yellow oil
Sources & evidence
- ORD record
- ord-2fc9af1643ca4223a61d71fb1628145a
- Source dataset
- uspto-grants-1977_08
- Patent number
- US04042373
Reaction notes
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