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

HRID 357104Notes

Reaction equation

HRID 357104 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=[C:10]2[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]3[N:26]4[CH:27]=[CH:28][N:29]=[C:25]4[CH:24]=[CH:23][CH:22]=3)[C:11]2=[O:30])[CH:2]=1.[ClH:31].C(OCC)(=O)C>CO>[ClH:31].[ClH:31].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=[C:10]2[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]3[N:26]4[CH:27]=[CH:28][N:29]=[C:25]4[CH:24]=[CH:23][CH:22]=3)[C:11]2=[O:30])[CH:2]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 571504255-[3-(3-Pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Product 1

HCID 867533485-[3-(3-Pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol solution of 1.56 g (3.6 mmol) of 5-[3-(3-pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione, 1.5 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 1.38 g (75.0%, 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-5debe6710e3142c687bad37f47d03a4f
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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