Water → 4-Bromo-5-(4-methyl-2-oxo-4-phenyl-valeroylamino)-phthalide

HRID 1266437Notes

Reaction equation

HRID 1266437 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH2:3][C:4](=[O:8])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[Br:20][C:21]1[C:30]([NH2:31])=[CH:29][CH:28]=[C:27]2[C:22]=1[CH2:23][O:24][C:25]2=[O:26].O>CC(N(C)C)=O>[Br:20][C:21]1[C:30]([NH:31][C:5](=[O:7])[C:4](=[O:8])[CH2:3][C:2]([CH3:1])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])=[CH:29][CH:28]=[C:27]2[C:22]=1[CH2:23][O:24][C:25]2=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 112411954-Methyl-2-oxo-4-phenylpentanoic acidHCID 185511684-Bromo-5-aminophthalide

Product 1

HCID 185512024-Bromo-5-(4-methyl-2-oxo-4-phenyl-valeroylamino)-phthalideYield 86.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

412 mg of 4-methyl-4-phenyl-2-oxovaleric acid is dissolved in 10 ml of dimethylacetamide and mixed under argon at −8° C. with 261 mg of thionyl chloride. After 20 minutes of stirring at −3 to +3° C., 228 mg of 4-bromo-5-aminophthalide is added. It is stirred for 1.5 hours at room temperature, then mixed with water, extracted with ethyl acetate, the organic phase is washed with water, dried (Na2SO4) and after the solvent is concentrated by evaporation and after treatment with diethyl ether, 360 mg of 4-bromo-5-(4-methyl-2-oxo-4-phenyl-valeroylamino)-phthalide, melting point 150-152° C, is obtained.

Workup

  1. stirringIt is stirred for 1.5 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationafter the solvent is concentrated by evaporation

Sources & evidence

ORD record
ord-12d0f1e6b96a4ae9a53e40de27b501e3
Source dataset
uspto-grants-2003_04
Patent number
US06548534B2

Reaction notes

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