Sodium Hydroxide → HCID 19595593, compound

HRID 612519Notes

Reaction equation

HRID 612519 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10]/[C:9](=[C:12](/[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)\[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)/[C:8]1=[O:30])(=O)C.[OH-].[Na+]>C(O)C.O>[Cl:29][C:26]1[CH:25]=[CH:24][C:23](/[C:12](=[C:9]2\[C:8](=[O:30])[N:7]([CH2:6][CH2:5][OH:4])[CH2:11][CH2:10]\2)/[C:13]2[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9824895HCID 9824895, compound

Product 1

HCID 19595593HCID 19595593, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1 g (0.0022 mole) of (Z)-2-[3-[1-(4-chlorophenyl)-1-[4-(methylsulphonyl)phenyl]methylene]-2-oxo-pyrrolidin-1-yl]ethyl acetate are placed in solution in a mixture of 13 ml of ethanol and 11 ml of water and treated with 0.1 g (1.1 eq.) of sodium hydroxide. The medium is stirred at ambient temperature for 4 h, then the ethanol is evaporated off. The aqueous phase is extracted with dichloromethane. The organic phase is washed with water, dried and concentrated. The residue is taken up into t-butyl methyl ether. 0.7 g of (Z)-3-[1-(4-chlorophenyl)-1-[4-(methylsulphonyl)phenyl]methylene]-1-(2-hydroxyethyl)-pyrrolidin-2-one are thus obtained as a yellow solid of melting point 187-188° C.

Workup

  1. customthe ethanol is evaporated off
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. washThe organic phase is washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-794833f1f50f40afa88cdfb983813347
Source dataset
uspto-grants-1999_12
Patent number
US06004994

Reaction notes

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