Hantzsch ester → HCID 21705023, compound

HRID 1595507Notes

Reaction equation

HRID 1595507 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH:19]=[C:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1)(=[O:4])=[O:3].C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C>>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 70849Hantzsch esterHCID 53906345HCID 53906345, compound

Product 1

HCID 21705023HCID 21705023, compoundYield 51%

Conditions

Temperature
150 °C

Procedure

1.63 g (3.2 mmole) 5-(4-[2-(2 methanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione and 1.23 g (4.8 mmole) diethyl-1,4-dihydro-2,6-dimethyl-3,5-pyridine dicarboxylate was mixed and heated to 150° C. and kept at this temperature for 1 hour. The reaction mixture was cooled and purified by chromatography on silica gel using ethyl acetate:petroleum ether (1:2) as eluent to give 0.684 g (yield 51%) of the desired product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-a101677fa571469fa715450a8213468c
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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