Acetic Acid → HCID 54069217, compound

HRID 1595545Notes

Reaction equation

HRID 1595545 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)[CH:7]=1)(=[O:4])=[O:3].[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]=[C:27]3[S:23][C:24](=[O:29])[NH:25][C:26]3=[O:28])=[CH:19][CH:20]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21704999HCID 21704999, compound

Product 1

HCID 54069217HCID 54069217, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

5.31 g (16.6 mmole) 3-[2-(4-formylphenoxy)ethyl]phenyl methanesulfonate, 2.13 g (18.2 mmole) 2,4-thiazolidinedione, 0.5 ml piperidine and 0.5 ml acetic acid in 300 ml toluene were 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 off and washed with diethyl ether to give 3.6 g (yield 51%) of 5-(4-[2-(3-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 off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-7c4ab55cfb7d40f99e68a46ba60cfb1b
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

Loading…