Sodium Hydroxide → 3-[(Phenylsulfonyl)amino]-2-thiophenecarboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])=[O:4].[OH-].[Na+]>C(#N)C>[C:14]1([S:11]([NH:10][C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([OH:4])=[O:2])(=[O:13])=[O:12])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
3-Benzenesulfonylaminothiophene-2-carboxylic acid methyl ester (1.5 g, 5.0 mmol) was dissolved in acetonitrile (10 mL) and treated with aqueous, sodium hydroxide solution (2N, 7.5 mL, 3 equivalents) at room temperature. The solution was warmed to 50° C. and monitored by thin layer chromatography. Upon completion of the reaction, the mixture was cooled and extracted once with diethyl ether. The ether layer was set aside. The aqueous layer was then acidified with aqueous HCl (2N, excess) before re-extracting twice with ethyl acetate. The combined organic layers were washed once with brine solution and dried over anhydrous sodium sulfate. The ethyl acetate was decanted and evaporated under reduced pressure to give of 3-benzenesulfonylaminothiophene-2-carboxylic acid (1.34 g, 95%) as a white powder.
Workup
- customUpon completion of the reaction
- temperaturethe mixture was cooled
- extractionextracted once with diethyl ether
- extractionbefore re-extracting twice with ethyl acetate
- washThe combined organic layers were washed once with brine solution
- dry with materialdried over anhydrous sodium sulfate
- customThe ethyl acetate was decanted
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-bd9a0798d0ad4eb6b944f69005b9728b
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07288538B2
Reaction notes
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