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

HRID 14589
Notes
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Reaction equation

HRID 14589 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-359696935bbe465abbd89b8f25825cb3
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732452B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes