Dimethylformamide → 5-Chloro-3-(4-methoxy-3-methylphenyl)-1-methyl-1H-pyrazole-4-carboxaldehyde
Reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[N:11]([CH3:12])[N:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH3:21])[CH:14]=2)[CH:8]=1.CN(C)[CH:24]=[O:25]>>[Cl:3][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH3:21])[CH:14]=2)[C:8]=1[CH:24]=[O:25]Participants
Procedure
At 0° C., to phosphorus oxychloride 56 g was added N,N-dimethylformamide 4.0 g and the resulting mixture was stirred for a half hour. Thereto was added 5-hydroxy-3-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole (described in Reference preparation example 90) 9.3 g. The resulting mixture was stirred for seven hours and the reaction solvent was distilled off under reduced pressure. To the reaction mixture was added ice water 100 ml and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 5-chloro-4-formyl-3-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole 6.3 g.
Workup
- stirringThe resulting mixture was stirred for seven hours
- distillationthe reaction solvent was distilled off under reduced pressure
- additionTo the reaction mixture was added ice water 100 ml
- extractionthe resulting mixture was extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialwas dried over anhydrous magnesium sulfate
- concentrationwas then concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-107677c1630e44d59c42b67ae1654029
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09314023B2
Reaction notes
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