Hantzsch ester → 5-([4-[2-(4-Methanesulfonylaminophenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dione

HRID 1595500Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH:19]=[C:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C>C1(C)C=CC=CC=1>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH2:19][CH:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[CH:17][CH:16]=2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 145 °C

Procedure

0.83 g (2 mmole) 5-(4-[2-(4-methanesulfonylaminophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione and 0.65 g (2.6 mmole) diethyl-1,4-dihydro-2,6-dimethyl-3.5-pyridinedicarboxylate was mixed and heated to 145° C. under vacuum. After 45 minutes at 145° C. the reaction mixture was taken off the heat and toluene was added. The toluene solution was decanted off and the solid residue was purified by chromatography on silica gel using dichloromethane:methanol 95:5 as eluent to give 0.25 g (yield 30%) of the desired product.

Workup

temperaturethe heat
customThe toluene solution was decanted off
customthe solid residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-bb6da079d5ea4d7c9f1052b9ae59c181
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288096B1

Reaction notes

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