Hydrochloric Acid → HCID 178437605, compound
Reaction equation
[CH2:1]([C:3]1[S:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[C:11]([O:22]COC)=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH3:21])[CH:14]=2)[N:7]=1)[CH3:2].Cl>CO>[CH2:1]([C:3]1[S:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[C:11]([OH:22])=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH3:21])[CH:14]=2)[N:7]=1)[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-ethyl-4-{(E)-2-[3-(methoxymethoxy)-1-(2-methylphenyl)-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole (0.81 g) in methanol (20 mL) was added concentrated hydrochloric acid (0.42 mL) at room temperature, and the mixture was stirred at 50° C. for 1 hr. The reaction mixture was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. Recrystallization of the residue from tetrahydrofuran-hexane gave 4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-(2-methylphenyl)-1H-pyrazol-3-ol (0.607 g, yield 86%) as colorless prism crystals. melting point: 174-176° C.
Workup
- customThe reaction mixture was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate
- additionwas added to the residue
- extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customRecrystallization of the residue from tetrahydrofuran-hexane
Sources & evidence
- ORD record
- ord-a69e34bd97ea4c058ed7eaa545cbd396
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368578B2
Reaction notes
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