Leriglitazone → 2,4-Thiazolidinedione, 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-, hydrochloride (1:1)

HRID 1756627Notes

Reaction equation

HRID 1756627 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][O:12][C:13]2[CH:26]=[CH:25][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:15][CH:14]=2)=[N:8][CH:9]=1)[CH3:3].[ClH:27].C(O)C>>[ClH:27].[OH:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][O:12][C:13]2[CH:26]=[CH:25][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:15][CH:14]=2)=[N:8][CH:9]=1)[CH3:3]

Participants

3

Reactant 2

HCID 4147757LeriglitazoneHCID 21887872Ethanol hydrochloride

Product 1

HCID 867488892,4-Thiazolidinedione, 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-, hydrochloride (1:1)Yield 62%

Procedure

5-[4-[2-[5-(1-Hydroxyethyl)-2-pyridyl]ethoxy]benzyl]-2,4-thiazolidinedione (0.3 g) was dissolved in hydrogen chloride-ethanol (25%, 1 ml). The solution was stirred at room temperature for 30 minutes and precipitated crystals were filtered off. The crystals were recrystallized from ethanol to obtain 5-[4-[2-[5-(1-hydroxyethyl)-2-pyridyl]ethoxy]benzyl]-2,4-thiazolidinedione hydrochloride (0.21 g, yield: 62%) as colorless prisms, m.p. 212°-213° C.

Workup

  1. customprecipitated crystals
  2. filtrationwere filtered off
  3. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-def00a45cc1a4e15a49aef749c4b1a78
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

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