Thionyl Chloride → HCID 86645104, compound
Reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([C:12](O)=[O:13])[C:3]1=[O:15].S(Cl)([Cl:18])=O>>[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([C:12]([Cl:18])=[O:13])[C:3]1=[O:15]Participants
Procedure
1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carboxylic acid (17.8 g, 80.5 mmol) was dissolved in thionyl chloride (70 mL), and this mixed solution was refluxed for 2 hours. The reaction solution was concentrated under reduced pressure to obtain 1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carbonyl chloride. The obtained acid chloride was dissolved in acetonitrile (80 mL), and added dropwise to a mixed solution of 5-hydroxy-1-methyl-1H-pyrazole hydrochloride (10.8 g, 80.3 mmol), triethylamine (20.4 g, 201 mmol) and acetonitrile (20 mL), under ice cooling. After stirring this mixed solution for a day at room temperature, acetonecyanhydrin (0.69 g, 8.05 mmol) and triethylamine (9.8 g, 96.6 mmol) were added thereto, and the mixture was stirred overnight at room temperature. To a residue obtained by concentrating the reaction solution under reduced pressure, a mixture of aqueous saturated sodium bicarbonate and ethyl acetate was added for extraction and separation. Thus obtained aqueous layer was added with diluted hydrochloric acid to give a pH of 3 to 4, and extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate, and the inorganic substance was separated by filtration. The solvent was distilled off under reduced pressure to obtain 10.4 g of a crude product of a subject compound.
Workup
- temperaturethis mixed solution was refluxed for 2 hours
- concentrationThe reaction solution was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-7bed83e3e6844d54aae963ed900de521
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076487B2
Reaction notes
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