Acetic Acid → 4-(i-Propylsulfonyl)-3-hydroxy-1-(4-thiophene-3-ylphenyl)-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-one

HRID 2037193Notes

Reaction equation

HRID 2037193 reaction equation
[CH:1]([S:4]([CH2:7][C:8](=[O:13])[C:9]([O:11]C)=O)(=[O:6])=[O:5])([CH3:3])[CH3:2].[S:14]1[CH:18]=[CH:17][C:16]([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)=[CH:15]1.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH:30]=O.C(O)(=O)C>CCOCC.C1(C)C=CC=CC=1>[CH:1]([S:4]([C:7]1[CH:30]([C:29]2[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=2[O:27][CH3:26])[N:23]([C:22]2[CH:24]=[CH:25][C:19]([C:16]3[CH:17]=[CH:18][S:14][CH:15]=3)=[CH:20][CH:21]=2)[C:9](=[O:11])[C:8]=1[OH:13])(=[O:5])=[O:6])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 86582-MethoxybenzaldehydeHCID 41303364-(Thiophen-3-yl)anilineHCID 58365407Methyl 3-(i-propylsulfonyl)-2-oxopropanoate

Product 1

HCID 583653164-(i-Propylsulfonyl)-3-hydroxy-1-(4-thiophene-3-ylphenyl)-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-oneYield 79%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 3-(i-propylsulfonyl)-2-oxopropanoate (0.23 g, 1 mmol), 4-thiophene-3-ylaniline (0.18 g, 1 mmol), 2-methoxybenzaldehyde (0.14, 1 mmol), acetic acid (0.023 mL, 0.4 mmol) and toluene (3 mL) was heated at reflux overnight. After the reaction was completed, the reaction mixture was allowed to cool to room temperature. To the mixture was added ether and precipitated compound was collected by filtration. The resulting aimed compound was washed with ether/n-hexane solution to give 4-(i-propylsulfonyl)-3-hydroxy-1-(4-thiophene-3-ylphenyl)-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-one (0.37 g, yield: 79%) as pale brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customprecipitated compound
  4. filtrationwas collected by filtration
  5. washThe resulting aimed compound was washed with ether/n-hexane solution

Sources & evidence

ORD record
ord-b602de288ce0466ebacf50b38907cb85
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

Loading…