HCID 10113866, compound → HCID 22678029, compound

HRID 1837537Notes

Reaction equation

HRID 1837537 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][C:11]2([S:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[S:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:4][CH:3]=1>[Pd].CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]2([S:18]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)(=[O:20])=[O:19])[S:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 10113866HCID 10113866, compound

Product 1

HCID 22678029HCID 22678029, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A sample of 5-[3-(4-Chlorophenyl)prop-2-ynyl]-5-(4-methoxy-benzenesulfonyl)thiazolidine-2,4-dione (U.S. Pat. No. 5,605,918; February 1997; Wrobel, et al.) was hydrogenated in the presence of palladium on charcoal (10%) in methanol plus 2% water to give the title compound as a colorless glass, NMR (CDCl3) δ1.57 (m, 1H); 1.97(m, 1H); 2.20 (triplet of doublet), 1H); 2.45 (m, 1H); 2.61 (q, 2H); 3.92 (s, 3H); 7.0 (dd, 4H); 7.26 (d, 2H) 7.98 (d, 2H).

Sources & evidence

ORD record
ord-7a7015f3544848d1be01cff279b959a5
Source dataset
uspto-grants-2004_08
Patent number
US06784184B2

Reaction notes

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