Methyl 5-(2,4-dioxothiazolidin-5-ylidene)methyl-2-methoxybenzoate → Methyl 5-(2,4-dioxothiazolidin-5-yl)methyl-2-methoxy-benzoate

HRID 1857503Notes

Reaction equation

HRID 1857503 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])[S:3]1>[Pd].CN(C=O)C>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])[S:3]1

Participants

4

Reactant 1

HCID 54363563Methyl 5-(2,4-dioxothiazolidin-5-ylidene)methyl-2-methoxybenzoate

Product 1

HCID 9922178Methyl 5-(2,4-dioxothiazolidin-5-yl)methyl-2-methoxy-benzoateYield 61.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Methyl 5-(2,4-dioxothiazolidin-5-ylidene)methyl-2-methoxy-benzoate (9.52 g) was suspended into DMF (250 ml) and hydrogenated with 10% palladium/carbon (10.0 g) at room temperature under a hydrogen pressure of 3.5 kg/cm2. After the reaction, the solution was filtered and concentrated and water was added to the residue, which was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by means of silica gel column chromatography (developing solvent; methylene chloride:acetone=50:1) to obtain 5.88 g (61%) of aimed compound as an amorphous material. MS(m/z):295(M+)

Workup

  1. customAfter the reaction
  2. filtrationthe solution was filtered
  3. concentrationconcentrated
  4. additionwater was added to the residue, which
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by means of silica gel column chromatography (developing solvent; methylene chloride:acetone=50:1)

Sources & evidence

ORD record
ord-f64b2a174025410da19ae929f700bc02
Source dataset
uspto-grants-2000_11
Patent number
US06147101

Reaction notes

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