Thiazolidinedione → HCID 54436213, compound

HRID 1595485Notes

Reaction equation

[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)=[C:8]([O:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:7]=1)(=[O:4])=[O:3].[S:28]1[CH2:32][C:31](=[O:33])[NH:30][C:29]1=[O:34].C([O-])(=O)C.[Na+]>ClCCl>[CH3:27][S:24]([O:23][C:8]1[CH:7]=[C:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:11]=[CH:10][C:9]=1[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]=[C:32]2[S:28][C:29](=[O:34])[NH:30][C:31]2=[O:33])=[CH:19][CH:20]=1)(=[O:25])=[O:26]

Participants

Conditions

Temperature: 175 °C

Procedure

0.887 g (2.14 mmole) 4-[2-(4-formylphenoxy)ethyl]-3-(methylsulfonyloxy)phenyl methanesulfonate was dissolved in 8 ml dichloromethane. 0.314 g (2.68 mmole) 2,4-thiazolidinedione and 0.439 g (5.35 mmole) sodium acetate were added and everything was mixed together. The solvent was evaporated in vacuo and the mixture was heated under vacuum to 175° C. and kept at this temperature for 20 minutes (the mixture melted at ca. 100° C.). After cooling the reaction mixture was stirred in water and acetone. Acetic acid was added and the precipitate was collected by filtration, washed with acetone/water, pure water and dried to give 0.76 g (yield 69%) of 5-(4-[2-(2,4-dimethanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

additioneverything was mixed together
customThe solvent was evaporated in vacuo
temperatureAfter cooling the reaction mixture
additionAcetic acid was added
filtrationthe precipitate was collected by filtration
washwashed with acetone/water, pure water
customdried

Sources & evidence

ORD record: ord-64061ec2e40b422f80d85a0be26f324b
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288096B1

Reaction notes

Loading…