Hydrochloric Acid → (E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoic acid
Reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:37]=[CH:36][C:17]([CH2:18][N:19]4[CH:23]=[C:22](/[CH:24]=[CH:25]/[C:26]([O:28]CC)=[O:27])[C:21]([C:31]5[S:32][CH:33]=[CH:34][CH:35]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:37]=[CH:36][C:17]([CH2:18][N:19]4[CH:23]=[C:22](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])[C:21]([C:31]5[S:32][CH:33]=[CH:34][CH:35]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
After a mixture of ethyl(E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoate (1.25 g), 1N aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (5 ml), and ethanol (5 ml) was stirred at 50° C. for 2 hours, 1N hydrochloric acid (5 ml) was added to the mixture, and then the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless crystals were collected by filtration to obtain (E)-3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propenoic acid (970 mg, yield 82%). This was recrystallized from ethyl acetate-hexane. Melting point: 137˜138° C.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
- dry with materialdried (MgSO4)
- concentrationconcentrated
- filtrationThe resulting colorless crystals were collected by filtration
Sources & evidence
- ORD record
- ord-20e6165d43164e049264e20816c8b707
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179823B1
Reaction notes
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