Sodium Sulfite → (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-[(methylsulfonyl)methyl]phenyl)acrylamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25]SC)=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.Cl[C:29]1C=CC=C(C(OO)=O)C=1.[S:39]([O-:42])([O-])=[O:40].[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][S:39]([CH3:29])(=[O:42])=[O:40])=[CH:23][CH:24]=2)=[O:17])=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(methylthio)methyl]phenyl}acrylamide (600 mg), m-chloroperbenzoic acid (780 mg) and tetrahydrofuran (50 mL) was stirred at 0° C. for 20 min. A saturated aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was further stirred for 10 min. and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate, and then with saturated brine, dried (MgSO4) and concentrated. The obtained solid was recrystallized from acetone-hexane to give (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-[(methylsulfonyl) methyl]phenyl)acrylamide (490 mg, yield 75%) as colorless prism crystals. melting point: 251-252° C.
Workup
- stirringthe mixture was further stirred for 10 min.
- extractionextracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
- dry with materialwith saturated brine, dried (MgSO4)
- concentrationconcentrated
- customThe obtained solid was recrystallized from acetone-hexane
Sources & evidence
- ORD record
- ord-84d27d96890147c68d709c8dcc2a656c
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423159B2
Reaction notes
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