Sodium Acetate → HCID 60028532, compound

HRID 1805135Notes

Reaction equation

HRID 1805135 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:6][C:5]=1[C:18]([F:21])([F:20])[F:19])([O-:3])=[O:2].CC([O-])=O.[Na+]>C(OC(=O)C)(=O)C.O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:11](=[O:17])[CH2:12][CH2:13][C:14]2=[O:16])=[CH:6][C:5]=1[C:18]([F:21])([F:20])[F:19])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 59410119HCID 59410119, compound

Product 1

HCID 60028532HCID 60028532, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 4-(4-nitro-3-(trifluoromethyl)phenylamino)-4-oxobutanoic acid (1.1 g, 3.6 mmol) and NaOAc (1.62 g, 19.75 mmol) in acetic anhydride (15 mL) was stirred overnight at 80° C. The reaction mixture was diluted with water and extracted twice with dichloromethane. The organic layers were combined and washed with NaOH (1 N) until pH was 9. The organic layer was separated, dried with MgSO4, filtered and concentrated in vacuo to provide 1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine-2,5-dione (0.4 g, 39%). LC/MS: m/z 288.9 (M+H)+.

Workup

  1. extractionextracted twice with dichloromethane
  2. washwashed with NaOH (1 N) until pH was 9
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0c99133912d42a093a477dea94a956a
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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