HCID 54002974, compound → 5-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-N-{[4-(trifluoromethyl)phenyl]methyl}benzamide

HRID 378346Notes

Reaction equation

HRID 378346 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:28]=[CH:27][C:6]([CH2:7][NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])[CH:13]=[CH:12][C:11]=2[O:24][CH3:25])=[CH:5][CH:4]=1>[Pd].C(O)C>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])[CH:13]=[CH:12][C:11]=2[O:24][CH3:25])=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 54002974HCID 54002974, compound

Product 1

HCID 1511835-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-N-{[4-(trifluoromethyl)phenyl]methyl}benzamideYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(4-Trifluoromethylbenzyl)-5-(2,4-dioxothiazolidin-5-ylidene)methyl-2-methoxybenzamide (500 mg) was suspended into ethanol (70 ml) and hydrogenated with 10% palladium/carbon (500 mg) at room temperature under a hydrogen pressure of 3.0 kg/cm2. The reaction liquor was filtered and concentrated and the residue was purified by means of silica gel column chromatography (developing solvent; methylene chloride:methanol=50:1) to obtain 403 mg (80%) of aimed compound as crystals. Further, these were recrystallized from ethyl acetate to obtain purified aimed compound as colorless powdery crystals. Melting point 176.0~177.5° C.

Workup

  1. filtrationThe reaction liquor was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by means of silica gel column chromatography (developing solvent; methylene chloride:methanol=50:1)

Sources & evidence

ORD record
ord-38cc7733fdd7466fb4aa3ba0fb2e8a32
Source dataset
uspto-grants-2000_02
Patent number
US06030990

Reaction notes

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