Triethylamine → HCID 86680350, compound
Reaction equation
CC1[N:3]([C:8]2[CH:12]=[C:11]([I:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:9]=2)C(C)=CC=1.[Cl-].O[NH3+].C(N(CC)CC)C>C(O)C.O>[I:13][C:11]1[N:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]=[C:8]([NH2:3])[CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To a solution of 3-(2,5-dimethylpyrrol-1-yl)-5-iodo-1-phenyl-1H-pyrazole (12.2 g) in ethanol/water (2/1, 180 ml) were sequentially added hydroxylammonium chloride (46.6 g) and triethylamine (9.3 ml), and the mixture was stirred at 95° C. for 72 hours. This reaction mixture was cooled to room temperature, and concentrated under reduced pressure. To the resulting residue was added a 8M aqueous solution of sodium hydroxide (80 ml), and then the mixture was extracted with ethyl acetate (50 ml). This organic layer was sequentially washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1) to give the titled compound (9.1 g).
Workup
- temperatureThis reaction mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- additionTo the resulting residue was added a 8M aqueous solution of sodium hydroxide (80 ml)
- extractionthe mixture was extracted with ethyl acetate (50 ml)
- 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=3/1)
Sources & evidence
- ORD record
- ord-3b559981b8ff45abad260a57d7f1766a
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846746B2
Reaction notes
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