Sodium Acetate → 2,5-Pyrrolidinedione, 3-methylene-1-phenyl-

HRID 271245Notes

Reaction equation

HRID 271245 reaction equation
[C:1]1([NH:7][C:8]([CH2:10][C:11](=[CH2:15])[C:12](O)=[O:13])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])=O.[Na+]>CC(OC(C)=O)=O>[CH2:15]=[C:11]1[CH2:10][C:8](=[O:9])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 219355602-[(N-phenylcarbamoyl)methyl]prop-2-enoic acid

Product 1

HCID 131082272,5-Pyrrolidinedione, 3-methylene-1-phenyl-

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
89 °C

Procedure

A suspension of the 2-[(N-phenylcarbamoyl)methyl]prop-2-enoic acid (700 mg, 3.41 mmol) in Ac2O (15 mL) was then treated with NaOAc (327 mg, 3.98 mmol) and shaken for 14 hours at 89° C. The resulting clear solution was dried on a Savant™, dissolved in EtOAc and washed with H2O and brine. The organic layers were then dried down on Savant™ to yield 3-methylene-1-phenylazolidine-2,5-dione, a compound of formula (7′).

Workup

  1. customThe resulting clear solution was dried on a Savant™
  2. dissolutiondissolved in EtOAc
  3. washwashed with H2O and brine
  4. customThe organic layers were then dried down on Savant™

Sources & evidence

ORD record
ord-5e07e49a88eb4e46bf610a4d3b166145
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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