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

HRID 14589

반응식

HRID 14589 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-359696935bbe465abbd89b8f25825cb3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732452B2

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