Water → HCID 69497924, compound

HRID 460666Notes

Reaction equation

HRID 460666 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH:5]=[C:6]1[CH2:10][CH2:9][NH:8][C:7]1=[O:11].[H-].[Na+].[CH3:18][O:19][CH2:20][CH2:21]Cl.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH:5]=[C:6]1[CH2:10][CH2:9][N:8]([CH2:21][CH2:20][O:19][CH3:18])[C:7]1=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 2641593-(2'-Methoxybenzylidene)-2-pyrrolidone

Product 1

HCID 69497924HCID 69497924, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The intermediate 3-(2′-methoxybenzylidene)-2-pyrrolidone (5.0 g) obtained in Example 317 was dissolved in dimethylformamide (50 ml) and sodium hydride (0.99 g) was added under ice-cooling. The mixture was stirred at room temperature for 30 min. To the reaction mixture was again added 2-methoxyethyl chloride (2.3 ml) under ice-cooling, and the mixture was stirred at room temperature for 1 hr and at 70° C. for 1 hr. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oily title compound (2.8 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 1 hr and at 70° C. for 1 hr
  4. temperatureAfter cooling
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f4d75ed6b214df99216f686092b13cf
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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