Acetic Acid → 5-[4-(3-Oxopropoxy)benzyl]thiazolidine-2,4-dione

HRID 1601876Notes

Reaction equation

[O:1]1CCO[CH:2]1[CH2:6][CH2:7][O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][CH:14]2[S:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:11][CH:10]=1.C(O)(=O)C>O>[O:1]=[CH:2][CH2:6][CH2:7][O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][CH:14]2[S:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 6.30 g of 5-{4-[2-(1,3-dioxolan-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione (prepared as described in Preparation 106) in 50 ml of a 4:1 mixture of acetic acid and water was stirred at 60° C. for 6 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.20 g of the title compound, melting at 48-51° C.

Workup

distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
customThe resulting residue was purified by column chromatography through silica gel
additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-184f599d6b834cafa4e84c127d979677
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977365

Reaction notes

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