4'-Hydroxyacetophenone → 5-(4-{2-[1-(4-Hydroxyphenyl)ethylideneaminooxy]ethoxy}benzyl)thiazolidine-2,4-dione

HRID 1941677Notes

Reaction equation

HRID 1941677 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.Cl.[NH2:12][O:13][CH2:14][CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:12][O:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:29][CH:30]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 74694'-HydroxyacetophenoneHCID 218339655-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride

Product 1

HCID 1363959675-(4-{2-[1-(4-Hydroxyphenyl)ethylideneaminooxy]ethoxy}benzyl)thiazolidine-2,4-dioneYield 84.2%

Procedure

Following a procedure similar to that described in Example 40(f), but using 0.33 g of 4'-hydroxyacetophenone and 0.70 g of 5-[4-(2-aminooxyethoxy)benzyl]-thiazolidine-2,4-dione hydrochloride [prepared as described in Example 40(e)], 0.74 g of the title compound, melting at 157°-159° C., was obtained.

Sources & evidence

ORD record
ord-90c8788440504ba1936d0bba5224b184
Source dataset
uspto-grants-1997_12
Patent number
US05703096

Reaction notes

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