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

HRID 2105277ノート

反応式

HRID 2105277 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9bdb28a1e86d44ba9973fa763319066c
出典データセット
uspto-grants-2009_08
特許番号
US07579340B2

反応ノート

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