Thiazolidinedione → 5-(3'-Methylaminobiphenyl-4-ylmethylene)thiazolidine-2,4-dione

Reaction equation

[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23]>>[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH:15]=[C:21]3[S:17][C:18](=[O:23])[NH:19][C:20]3=[O:22])=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 5437Thiazolidinedione

HCID 13945243'-Methylaminobiphenyl-4-carbaldehyde

Product 1

HCID 865989415-(3'-Methylaminobiphenyl-4-ylmethylene)thiazolidine-2,4-dioneYield 91.7%

Procedure

In a manner similar to that of Example 1(f), starting with 2.9 g (13.7 mmol) of 3′-methylaminobiphenyl-4-carboxaldehyde and 1.6 g (13.7 mmol) of 2,4-thiazolidine dione, 3.9 g (91%) of the expected product are obtained.

Sources & evidence

ORD record: ord-1b9881585c8f4effb24e41666e74170b
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06927228B2

Reaction notes

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