Hydrochloric Acid → 5-(4-Methoxyphenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]([O:16]C)=[O:15])=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[CH:20][CH:19]=3)[C:10]=2[CH3:28])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]([C:14]([OH:16])=[O:15])=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[CH:20][CH:19]=3)[C:10]=2[CH3:28])=[CH:7][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 52.5 °C
Procedure
Methyl 5-(4-methoxyphenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylate (compound 7d, 3.02 g, 7.24 mmol) was suspended in ethanol (50 ml) and NaOH (1.44 g, 36.2 mmol) in water 10 ml was added at 25° C. The reaction mixture was heated at 50-55° C. under stirring for 2 hr. The progress of reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. Water, 50 ml was added to the residue so obtained and the mixture was cooled using icebath. Aqueous hydrochloric acid (10%) was then added to the mixture to bring the pH to between 5 and 6. The mixture was then extracted with ethyl acetate (2×75 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain a product (2.83 g, 97%).
Workup
- customThe progress of reaction
- concentrationThe reaction mixture was then concentrated under reduced pressure
- additionWater, 50 ml was added to the residue
- customso obtained
- temperaturethe mixture was cooled
- extractionThe mixture was then extracted with ethyl acetate (2×75 ml)
- dry with materialThe combined organic layer was dried over anhydrous Na2SO4
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-ae3893fea054403ba5f8289f335455b0
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09072731B2
Reaction notes
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