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

HRID 357208Notes

Reaction equation

HRID 357208 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=[C:11]2[S:15][C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][S:21][C:22]3[N:27]4[CH:28]=[CH:29][N:30]=[C:26]4[CH:25]=[CH:24][CH:23]=3)[C:12]2=[O:31])=[CH:4][CH:3]=1.[ClH:32].C(OCC)(=O)C>CO>[ClH:32].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH:10]=[C:11]2[S:15][C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][S:21][C:22]3[N:27]4[CH:28]=[CH:29][N:30]=[C:26]4[CH:25]=[CH:24][CH:23]=3)[C:12]2=[O:31])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 572946405-[3-(4-Fluorophenyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Product 1

HCID 867533525-[3-(4-Fluorophenyl)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 0.88 g (1.9 mmol) of 5-[3-(4-fluorophenyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione, 1.0 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 hexane to yield 0.78 g (83.1%, white crystal) of the desired product.

Workup

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

Sources & evidence

ORD record
ord-00c27dfd2458436f85f2b32e276651ed
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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