Sodium Hydroxide → 3-[(Phenylsulfonyl)amino]-2-thiophenecarboxylic acid

HRID 2251312Notes

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]=1

Participants

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-18f7c21ec5ae484cbb6243aed424f92b
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319111B2

Reaction notes

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