Hantzsch ester → HCID 21705021, compound

HRID 1595549Notes

Reaction equation

HRID 1595549 reaction equation
[F:1][C:2]([F:31])([F:30])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15][C:16]2[CH:29]=[CH:28][C:19]([CH:20]=[C:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C>>[F:31][C:2]([F:1])([F:30])[S:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:28][CH:29]=2)=[CH:11][CH:12]=1)(=[O:5])=[O:4]

Participants

3

Reactant 2

HCID 70849Hantzsch esterHCID 53634277HCID 53634277, compound

Product 1

HCID 21705021HCID 21705021, compoundYield 38.3%

Conditions

Temperature
180 °C

Procedure

2 g (4.22 mmole) 5-(4-[2-(4-trifluoromethanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione and 2.14 g (8.44 mmole) diethyl-1,4-dihydro-2,6-dimethyl-3.5-pyridine dicarboxylate were mixed and heated to 180° C. under vacuum when it melted, the temperature raised to 230° C. and after 30 minutes the heat was removed. Purification by chromatography on silica gel with heptane/ethyl acetate as eluent gave 0.768 g (yield 38%) of the desired product.

Workup

  1. temperaturethe temperature raised to 230° C. and after 30 minutes the heat
  2. customwas removed
  3. customPurification by chromatography on silica gel with heptane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-9f5da8fc9faa49c79419517d148f93e1
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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