Water → 5-[4-(4-Iodo-2-methoxyphenyl)-4-methyl-2-oxo-valeroylamino)-phthalide

HRID 430469Notes

Reaction equation

HRID 430469 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][C:10](=[O:14])[C:11]([OH:13])=O)=[C:4]([O:17][CH3:18])[CH:3]=1.S(Cl)(Cl)=O.[NH2:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:29](=[O:30])[O:28][CH2:27]2.O>CC(N(C)C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][C:10](=[O:14])[C:11]([NH:23][C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[C:29](=[O:30])[O:28][CH2:27]3)=[O:13])=[C:4]([O:17][CH3:18])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 7206695-AminophthalideHCID 185511904-(4-Iodo-2-methoxyphenyl)-4-methyl-2-oxovaleric acid

Product 1

HCID 183506275-[4-(4-Iodo-2-methoxyphenyl)-4-methyl-2-oxo-valeroylamino)-phthalideYield 64.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.7 g of 4-(4-iodo-2-methoxyphenyl)-4-methyl-2-oxo-valeric acid is dissolved in 25 ml of dimethyl acetamide and mixed under argon at −8° C. with 0.37 ml of thionyl chloride. After 20 minutes of stirring at −3 to +3° C., 700 mg of 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 chromatography of the crude product on silica gel with hexane/ethyl acetate (80:20), 1.5 g of 5-[4-(4-iodo-2-methoxyphenyl)-4-methyl-2-oxo-valeroylamino)-phthalide is obtained as a foam.

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-9469fbba28ea437b877e3683a8b89642
Source dataset
uspto-grants-2001_11
Patent number
US06323199B1

Reaction notes

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