Water → HCID 14856958, compound

HRID 1031118Notes

Reaction equation

HRID 1031118 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10](=[O:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:20][C:21](OCC)=[O:22].O>CN(C=O)C>[C:3]1([N:9]2[CH2:20][C:21](=[O:22])[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]2=[O:18])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 225533N,2-Diphenylacetamide

Product 1

HCID 14856958HCID 14856958, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred slurry of 500 mg (12 mmol) of a 60% oil dispersion of sodium hydride (which had been washed with hexane) in 12 ml dry DMF under argon atmosphere was added 1.06 g (5.0 mmol) of N-phenyl-2-phenyl acetamide (IVa) in 5 mL dry DMF. Gas evolution had ceased after 30 minutes and 0.560 mL (5.0 mmol) of ethyl bromoacetate was added via syringe. The solution was stirred at 25° C. for 30 minutes, then warmed to 80° C. for 4 hours. The cooled solution was carefully poured into 200 mL H2O, washed with ether, filtered over celite and acidified to pH=2. The white precipitate was filtered, washed well with H2O and dried under high vacuum to give 1.04 g (4.0 mmol, 80% yield) of 1,3-diphenyl-2,4-pyrrolidinedione Ia, mp 285°-287° C.

Workup

  1. temperaturewarmed to 80° C. for 4 hours
  2. washwashed with ether
  3. filtrationfiltered over celite
  4. filtrationThe white precipitate was filtered
  5. washwashed well with H2O
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-15e59d10df764572b8f3fce88d448a40
Source dataset
uspto-grants-1992_04
Patent number
US05109010

Reaction notes

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