Hydrogen Peroxide → ethyl 2-(4-carbamoyl-2-methylphenyl)-1-(4-chloro-2-methoxyphenyl)-1H-pyrrole-3-carboxylate

HRID 238406Notes

Reaction equation

HRID 238406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]2[C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=2[CH3:26])=[C:4]([O:27][CH3:28])[CH:3]=1.[OH-].[Na+].OO.CC[O:35]C(C)=O>CS(C)=O.CO>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:9]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=3[O:27][CH3:28])[CH:12]=[CH:11][C:10]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:19]([CH3:26])[CH:20]=1)(=[O:35])[NH2:25]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67176185HCID 67176185, compound

Product 1

HCID 67176148ethyl 2-(4-carbamoyl-2-methylphenyl)-1-(4-chloro-2-methoxyphenyl)-1H-pyrrole-3-carboxylateYield 23.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To a solution of ethyl 1-(4-chloro-2-methoxyphenyl)-2-(4-cyano-2-methylphenyl)-1H-pyrrole-3-carboxylate (5.0 g, 12.7 mmol) in DMSO (10 mL) was added aqueous NaOH solution (2 mol/L, 1.0 mL) and 30% aqueous solution of H2O2 (1.0 mL), the reaction mixture was stirred at room temperature for four hours. TLC (EtOAc: MeOH=10:1) indicated that the starting material was consumed. Saturated aqueous Na2SO3 solution was added to quench the reaction, and the aqueous layer was extracted with EtOAc (20 mL×3). The combined organic layer was washed with brine (20 mL), dried over Na2SO4, filtered, concentrated, and purified by column chromatograph to afford the titled compound as a yellow oil (1.2 g, yield: 23.1%).

Workup

  1. customwas consumed
  2. additionSaturated aqueous Na2SO3 solution was added
  3. customto quench
  4. customthe reaction
  5. extractionthe aqueous layer was extracted with EtOAc (20 mL×3)
  6. washThe combined organic layer was washed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by column chromatograph

Sources & evidence

ORD record
ord-532139bd22c044c5a95134040df312c7
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

Loading…