HCID 73989463, compound → HCID 22494254, compound

HRID 1816580Notes

Reaction equation

HRID 1816580 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:29][CH3:30])=[C:13]([CH:28]=2)[CH2:14][NH:15][C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[S:3]1.[H][H]>CN(C)C=O.[C].[Pd]>[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:29][CH3:30])=[C:13]([CH:28]=2)[CH2:14][NH:15][C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=2)[S:3]1

Participants

5

Reactant 2

HCID 73989463HCID 73989463, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22494254HCID 22494254, compoundYield 217.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

0.55 g of N1-(5-[(2,4-dioxo-1,3-thiazolane-5-ylidene)methyl]-2-methoxybenzyl)-4-(trifluoromethyl)benzamide was suspended in 20 ml N,N-dimethylformamide, and 0.60 g of 10% palladium-carbon was added, and the mixture was stirred at 50° C. under pressure at 15 kg/cm2 hydrogen for 16 hours. After the reaction, the catalyst was filtered off, and after the solvent was evapoarated. Water was added to the residue, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (1:1), 1.2 g of N1-{5-[(2,4-dioxo-1,3-thiazolane-5-yl)methyl]-2-methoxybenzyl}-4-(trifluoromethyl)benzamide was obtained.

Workup

  1. customAfter the reaction
  2. filtrationthe catalyst was filtered off
  3. additionWater was added to the residue
  4. extractionby extracting with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washfrom fractions eluted with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-be647da5ede9422f9257a88e46238919
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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