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Potassium Carbonate → N-(4-((4-methoxyphenyl)sulfonyl)phenyl)-3-(pyridin-3-yl)acrylamide

HRID 1754111
Notes
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Reaction equation

HRID 1754111 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[CH:26][C:27](Cl)=[O:28])[CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[CH:18]=[CH:17][C:15]([NH:16][C:27](=[O:28])[CH:26]=[CH:25][C:21]3[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=3)=[CH:14][CH:13]=2)(=[O:10])=[O:11])=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5166674-(4-Methoxyphenyl)sulfonylanilineHCID 533991563-(Pyridin-3-yl)acryloyl chloride

Product 1

HCID 70979357N-(4-((4-methoxyphenyl)sulfonyl)phenyl)-3-(pyridin-3-yl)acrylamideYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-((4-methoxyphenyl)sulfonyl)aniline (76 mg, 0.29 mmol) in DMF (3 mL) is added 3-(pyridin-3-yl)acryloyl chloride (62 mg, 0.30 mmol) and K2CO3 (138 mg, 1 mmol). The mixture is heated at 50° C. for 2 h and the solvent is evaporated. The residue is partitioned between EtOAc (15 mL) and brine (10 mL) and the layers are separated. The aqueous layer is extracted with EtOAc (10 mL) and the combined extracts are dried (Na2SO4) and evaporated. Purification of the residue by preparative TLC with 100:5:0.5 CH2Cl2/MeOH/NH4OH gives the titled compounds as a white solid (66 mg, 58%).

Workup

  1. customthe solvent is evaporated
  2. customThe residue is partitioned between EtOAc (15 mL) and brine (10 mL)
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted with EtOAc (10 mL)
  5. dry with materialthe combined extracts are dried (Na2SO4)
  6. customevaporated
  7. customPurification of the residue by preparative TLC with 100:5:0.5 CH2Cl2/MeOH/NH4OH

Sources & evidence

ORD record
ord-84caccf37ae648af9649408e09087970
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09169209B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes