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

HRID 1595478Notes

Reaction equation

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

Participants

Conditions

Temperature: 210 °C

Procedure

3.9 g (11 mmole) 5-(4-[2-(4-cyanophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione and 3.88 g (15 mmole) diethyl-1,4-dihydro-2,6-dimethyl-3,5-pyridine dicarboxylate were mixed and heated to 210° C. under vacuum for 1 hour. The solid material was dissolved in ethyl acetate, evaporated in vacuo, purified by chromatography on silica gel with first dichloromethane, then dichloromethane:diethyl ether (95:5) and finally dichloromethane:methanol (95:5) as eluents. Crystallization in acetone/water gave 0.65 g (yield 17%) of the desired product.

Workup

customevaporated in vacuo
custompurified by chromatography on silica gel with first dichloromethane
customCrystallization in acetone/water

Sources & evidence

ORD record: ord-ac12f052937a499a86a0a40ccbe07b25
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288096B1

Reaction notes

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