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Acetic Acid → 5-(4-Methoxycarbonylmethyloxybenzyl)thiazolidine-2,4-dione

HRID 1419118
Notes
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Reaction equation

HRID 1419118 reaction equation
C(O)(=O)C.O.[CH3:6][O:7][C:8]([CH2:10][O:11][C:12]1[CH:44]=[CH:43][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:18]2=[O:42])=[CH:14][CH:13]=1)=[O:9]>O1CCOCC1>[CH3:6][O:7][C:8]([CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:42])=[CH:43][CH:44]=1)=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 221190505-(4-Methoxycarbonylmethoxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

Product 1

HCID 235141985-(4-Methoxycarbonylmethyloxybenzyl)thiazolidine-2,4-dioneYield 85.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1700 ml of acetic acid and then 400 ml of water were added at room temperature to a suspension of 344 g of 5-(4-methoxycarbonylmethoxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 20) in 400 ml of 1,4-dioxane and the resulting mixture was stirred for 5 hours at 80° C. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of ethyl acetate and hexane, a 2:1 by volume mixture of ethyl acetate and hexane and then ethyl acetate as eluents, to give 161.7 g of the title compound, melting at 100°-106° C.

Workup

  1. customAt the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure
  2. customthe resulting residue was purified by column chromatography through silica gel using a 1:2
  3. additionby volume mixture of ethyl acetate and hexane
  4. additiona 2:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-270938baee78417bb09893c1da11f76d
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05886014

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes