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

HRID 1595494Notes

Reaction equation

HRID 1595494 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: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]([O: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

4

Reactant 2

HCID 70849Hantzsch esterHCID 536855295-(4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

Product 1

HCID 217050165-([4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dioneYield 79.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

98 g (0.23 mole) 5-(4-[2-(4-methanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione and 89 g (0.35 mole) diethyl-1,4-dihydro-2,6-dimethyl-3,5-pyridine dicarboxylate was heated under reduced pressure until it melted (160° C.). The reaction mixture was allowed to stay at this temperature for 5 hours. The reaction mixture was then taken off the heat and toluene was added when the temperature was below 100° C. The crystals were collected and washed with diethyl ether and recrystallized in toluene to give 77 g (yield 79%) of the desired product.

Workup

  1. custom(160° C.)
  2. temperatureheat
  3. customwas below 100° C
  4. customThe crystals were collected
  5. washwashed with diethyl ether
  6. customrecrystallized in toluene

Sources & evidence

ORD record
ord-4b6890660f244b2fac5982bb71f10462
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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