4'-Hydroxy-3',5'-dimethylacetophenone → 5-(4-{2-[1-(4-Hydroxy-3,5-dimethylphenyl)ethylideneaminooxy]ethoxy}benzyl)thiazolidine-2,4-dione

HRID 1741341Notes

Reaction equation

HRID 1741341 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=O)[CH3:10])=[CH:4][C:3]=1[CH3:12].Cl.[NH2:14][O:15][CH2:16][CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:21][CH:20]=1>>[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=[N:14][O:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:31][CH:32]=2)[CH3:10])=[CH:4][C:3]=1[CH3:12]

Participants

3

Reactant 2

HCID 365814'-Hydroxy-3',5'-dimethylacetophenoneHCID 218339655-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride

Product 1

HCID 1363959695-(4-{2-[1-(4-Hydroxy-3,5-dimethylphenyl)ethylideneaminooxy]ethoxy}benzyl)thiazolidine-2,4-dioneYield 55.8%

Procedure

Following a procedure similar to that described in Example 46, but using 0.22 g of 4'-hydroxy-3',5'-dimethylacetophenone and 0.40 g of 5-[4-(2-aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride [prepared as described in Example 40(e)], 0.30 g of the title compound was obtained as an amorphous powder, melting at 53-65° C. (softening point).

Sources & evidence

ORD record
ord-e9520562171c483b9a61f0dea8302609
Source dataset
uspto-grants-1999_10
Patent number
US05972959

Reaction notes

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