Thiazolidinedione → Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]methylcarbamate

HRID 584906Notes

Reaction equation

HRID 584906 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]=2)=[CH:5][CH:4]=1)=O.[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31]>>[O:31]=[C:26]1[NH:27][C:28](=[O:30])[C:29](=[CH:1][C:3]2[CH:4]=[CH:5][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:10]=3)=[CH:7][CH:8]=2)[S:25]1

Participants

3

Reactant 2

HCID 5437ThiazolidinedioneHCID 86591268Tert-butyl (4'-formylbiphenyl-3-ylmethyl)methylcarbamate

Product 1

HCID 86598938Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]methylcarbamateYield 81%

Procedure

In a manner similar to that of Example 1(f), by reacting 8 g (25 mmol) of tert-butyl (4′-formyl-biphenyl-3-ylmethyl)methylcarbamate with 2.9 g (25 mmol) of 2,4-thiazolidine dione, 8.6 g (81%) of the expected product are obtained.

Sources & evidence

ORD record
ord-cecb532f2fc747c0a68a21c41568d842
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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