Phosphorus oxychloride → HCID 22320246, compound
Reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](O)=O)=[C:4]([NH:12][C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:16]=[C:15]([CH3:24])[CH:14]=2)[CH:3]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:6]1[C:5]2[C:4](=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=2)[N:12]=[C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:16]=[C:15]([CH3:24])[C:14]=12Participants
Procedure
A solution of 4,5-difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid (8.14 g, 24.6 mmol) in phosphorous oxychloride (13 mL, 138 mmol) was heated under reflux for 1.5 hours. The solution was cooled to room temperature and concentrated under reduced pressure, and the residue was poured into iced water. The solution was neutralized by the addition of a sodium hydroxide solution, and the organic matter was extracted with chloroform. The extract was washed with saturated brine and water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform) to give the title compound (4.42 g, 54% yield).
Workup
- temperatureunder reflux for 1.5 hours
- concentrationconcentrated under reduced pressure
- additionthe residue was poured into iced water
- additionThe solution was neutralized by the addition of a sodium hydroxide solution
- extractionthe organic matter was extracted with chloroform
- washThe extract was washed with saturated brine and water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue thus obtained
- customwas purified by silica gel column chromatography (chloroform)
Sources & evidence
- ORD record
- ord-d6b9d93185824aaeab47cbac075dcd90
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06949648B2
Reaction notes
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