Acetic Acid → 5-(4-[2-(4-Tert-butylaminocarbonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

HRID 1595516Notes

Reaction equation

HRID 1595516 reaction equation
[C:1]([NH:5][C:6](=[O:25])[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[S:26]1[CH2:30][C:29](=[O:31])[NH:28][C:27]1=[O:32].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[C:1]([NH:5][C:6]([O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH:23]=[C:30]3[S:26][C:27](=[O:32])[NH:28][C:29]3=[O:31])=[CH:21][CH:22]=2)=[CH:12][CH:13]=1)=[O:25])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 217049744-[2-(4-formylphenoxy)ethyl]phenyl N-(tert-butyl)carbamate

Product 1

HCID 542986395-(4-[2-(4-Tert-butylaminocarbonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dioneYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3.5 g (10.2 mmole) 4-[2-(4-formylphenoxy)ethyl]phenyl N-(tert-butyl)carbamate, 3 g (25.5 mmole) 2,4-thiazolidindione, 0.1 g piperidine and 0.07 g acetic acid in toluene was refluxed with water separation in a Dean-Stark apparatus. The solvent was evaporated in vacuo, acetone and water was added and the formed precipitate was filtered off to give 2 g (yield 45%) of 5-(4-[2-(4-tert-butylaminocarbonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. customThe solvent was evaporated in vacuo, acetone and water
  2. additionwas added
  3. filtrationthe formed precipitate was filtered off

Sources & evidence

ORD record
ord-9621847e352d4a6790f2afed5304c417
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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