Hydrochloric Acid → 5-(4-Methoxyphenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid

HRID 1518690ノート

反応式

HRID 1518690 の反応式
[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]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68285228Methyl 5-(4-methoxyphenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylate2 回

生成物 1

HCID 682852325-(4-Methoxyphenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylic acid収率 97%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
52.5 °C

実験手順

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%).

後処理

  1. customThe progress of reaction
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. additionWater, 50 ml was added to the residue
  4. customso obtained
  5. temperaturethe mixture was cooled
  6. extractionThe mixture was then extracted with ethyl acetate (2×75 ml)
  7. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  8. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-ae3893fea054403ba5f8289f335455b0
出典データセット
uspto-grants-2015_07
特許番号
US09072731B2

反応ノート

読み込み中…