Ethyl Acetate → 4-[2-(4-Iodo-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

HRID 14589

反応式

HRID 14589 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:15])[CH2:12]CCl)=[CH:8][S:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[I:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:15])[CH2:12][O:29][C:26]2[CH:27]=[CH:28][C:23]([I:22])=[CH:24][CH:25]=2)=[CH:8][S:7][CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 686867214-(3-Chloro-propionylamino)-thiophene-3-carboxylic acid methyl ester

生成物 1

HCID 686873304-[2-(4-Iodo-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester収率 99.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 4-(3-chloro-propionylamino)-thiophene-3-carboxylic acid methyl ester ([51486-30-7], 2.0 g, 8.6 mmol) in dimethylformamide (30 mL) was added potassium carbonate (1.77 g, 12.8 mmol) and 4-iodophenol (2.26 g, 10.3 mmol) and the reaction mixture was then stirred overnight at 90° C. To the reaction mixture was added ethyl acetate (approximately 30 mL). The solid was filtered and washed with ethyl acetate. The filtrate was then reduced in vacuo and dissolved in dichloromethane (approximately 50 mL). The solution was filtered again over charcoal and to the filtrate was added isopropylether. After reducing the solution slowly in vacuo the solid was filtered to yield the title compound (3.57 g, 79%).

後処理

  1. filtrationThe solid was filtered
  2. washwashed with ethyl acetate
  3. dissolutiondissolved in dichloromethane (approximately 50 mL)
  4. filtrationThe solution was filtered again over charcoal and to the filtrate
  5. additionwas added isopropylether
  6. filtrationwas filtered

出典と根拠

ORDレコード
ord-359696935bbe465abbd89b8f25825cb3
出典データセット
uspto-grants-2010_06
特許番号
US07732452B2

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