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

HRID 1182254노트

반응식

HRID 1182254 반응식
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

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 4430392methyl 3-[(phenylsulfonyl)amino]thiophene-2-carboxylate

생성물 1

HCID 167780913-[(Phenylsulfonyl)amino]-2-thiophenecarboxylic acid수율 95%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  1. customUpon completion of the reaction
  2. temperaturethe mixture was cooled
  3. extractionextracted once with diethyl ether
  4. extractionbefore re-extracting twice with ethyl acetate
  5. washThe combined organic layers were washed once with brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe ethyl acetate was decanted
  8. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-bd9a0798d0ad4eb6b944f69005b9728b
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288538B2

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