5-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride → 5-[4-(2-{1-[4-(4-Pyridylsulfonyl)phenyl]ethylideneaminooxy}ethoxy)benzyl]thiazolidine-2,4-dione

HRID 1741331Notes

Reaction equation

HRID 1741331 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=O)[CH3:17])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.Cl.[NH2:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:38]=[CH:37][C:28]([CH2:29][CH:30]2[S:34][C:33](=[O:35])[NH:32][C:31]2=[O:36])=[CH:27][CH:26]=1>>[N:1]1[CH:6]=[CH:5][C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[N:20][O:21][CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][C:28]([CH2:29][CH:30]4[S:34][C:33](=[O:35])[NH:32][C:31]4=[O:36])=[CH:37][CH:38]=3)[CH3:17])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 218339655-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochlorideHCID 218339951-[4-(Pyridine-4-sulfonyl)phenyl]ethan-1-one

Product 1

HCID 867518235-[4-(2-{1-[4-(4-Pyridylsulfonyl)phenyl]ethylideneaminooxy}ethoxy)benzyl]thiazolidine-2,4-dioneYield 57.3%

Procedure

Following a procedure similar to that described in Example 40(f), but using 150 mg of 4'-(4-pyridylsulfonyl)acetophenone and 183 mg of 5-[4-(2-aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride [prepared as described in Example 40(e)], 173 mg of the title compound, melting at 213-215° C., were obtained.

Sources & evidence

ORD record
ord-fa15214acfa440e1a5ae8a02b51a5de6
Source dataset
uspto-grants-1999_10
Patent number
US05972959

Reaction notes

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