Triethylamine → 1-(4-Chlorophenyl)-5-iodo-1H-pyrazol-3-ylamine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([I:13])=[CH:11][C:10]([N:14]3C(C)=CC=C3C)=[N:9]2)=[CH:4][CH:3]=1.[Cl-].O[NH3+].C(N(CC)CC)C>CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([I:13])=[CH:11][C:10]([NH2:14])=[N:9]2)=[CH:6][CH:7]=1Participants
Conditions
- Temperature
- 95 °C
Procedure
To a suspension of 1-(4-chlorophenyl)-3-(2,5-dimethylpyrrol-1-yl)-5-iodo-1H-pyrazole (4.19 g) in ethanol/water (2/1, 72 ml) were sequentially added hydroxylammonium chloride (14.64 g) and triethylamine (2.9 ml) at room temperature, and the mixture was stirred at 95° C. for 86 hours. This reaction mixture was cooled to room temperature, and concentrated under reduced pressure. To the resulting residue was added an 8M aqueous solution of sodium hydroxide, and then the mixture was extracted with ethyl acetate. This organic layer was sequentially washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give the titled compound (1.87 g).
Workup
- customat room temperature
- temperatureThis reaction mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- additionTo the resulting residue was added an 8M aqueous solution of sodium hydroxide
- extractionthe mixture was extracted with ethyl acetate
- washThis organic layer was sequentially washed with water
- dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)
Sources & evidence
- ORD record
- ord-cf7b21bbe8554e0b8e9a3106fcf278a4
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846746B2
Reaction notes
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