Acetic Acid → HCID 54051251, compound

HRID 1595541Notes

Reaction equation

HRID 1595541 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:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)=[CH:8][C:7]=1[O:23][CH3:24])(=[O:4])=[O:3].[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:24][O:23][C:7]1[CH:8]=[C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[C:29]3[S:25][C:26](=[O:31])[NH:27][C:28]3=[O:30])=[CH:17][CH:16]=2)[CH:10]=[CH:11][C:6]=1[O:5][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21704994HCID 21704994, compound

Product 1

HCID 54051251HCID 54051251, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

34 g (97 mmole) 4-[2-(4-formylphenoxy)ethyl]-2-methoxyphenyl methanesulfonate, 12.5 g (107 mmole) 2,4-thiazolidinedione, 0.5 ml piperidine and 0.5 ml acetic acid in 500 ml toluene was refluxed with water separation in a Dean-Stark apparatus for 4 hours. The solvent was evaporated, acetic acid was added and the mixture was heated. The formed precipitate was filtered and washed with diethyl ether to give 31.5 g (yield 72%) of 5-(4-[2-(3-methoxy-4-methanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. customThe solvent was evaporated
  2. additionacetic acid was added
  3. temperaturethe mixture was heated
  4. filtrationThe formed precipitate was filtered
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c3e5cdb373a44e03aecd40aff36846e5
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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