Hydrogen chloride-ethyl acetate → 5-[3-(4-Methoxyphenyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione hydrochloride

HRID 357204Notes

Reaction equation

HRID 357204 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]=[C:12]2[S:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][S:22][C:23]3[N:28]4[CH:29]=[CH:30][N:31]=[C:27]4[CH:26]=[CH:25][CH:24]=3)[C:13]2=[O:32])=[CH:5][CH:4]=1.[ClH:33].C(OCC)(=O)C>CO>[ClH:33].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11]=[C:12]2[S:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][S:22][C:23]3[N:28]4[CH:29]=[CH:30][N:31]=[C:27]4[CH:26]=[CH:25][CH:24]=3)[C:13]2=[O:32])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 572983275-[3-(4-Methoxyphenyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-yl-thio)butyl]thiazolidine-2,4-dione

Product 1

HCID 734729365-[3-(4-Methoxyphenyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol solution of 1.08 g (2.3 mmol) of 5-[3-(4-methoxyphenyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione, 0.8 ml of 4N hydrochloric acid-ethyl acetate was added, followed by stirring. After the solvent was distilled off, the residue was dissolved in methanol and recrystallized from ether to yield 995 mg (85.6%, white crystal) of the desired product.

Workup

  1. distillationAfter the solvent was distilled off
  2. dissolutionthe residue was dissolved in methanol
  3. customrecrystallized from ether

Sources & evidence

ORD record
ord-b7587759399b40118d1d0bcf4af57313
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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