Hydrochloric Acid → HCID 11268957, compound

HRID 1789172Notes

Reaction equation

HRID 1789172 reaction equation
N=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)=[CH:11][CH:10]=2)[S:3]1.Cl.C(=O)([O-])[OH:27].[Na+]>C(O)C>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]([CH2:8][CH:4]3[S:3][C:2](=[O:27])[NH:6][C:5]3=[O:7])=[CH:10][CH:11]=2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 140346828HCID 140346828, compound

Product 1

HCID 11268957HCID 11268957, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-imino-5-{4-[2-(5-methyl-2-pyridyl)ethoxy]benzyl}-4-thiazolidinone (8.0 g), 2N HCl (80 ml) and ethanol (80 ml) was refluxed for 16 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium hydrogencarbonate to yield crystals. The crystals were collected by filtration and recrystallized from ethanol to give 5-{4-[2-(5-methyl-2pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione as colorless prisms (7.0 g, 87.5%), m.p. 192°-193° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customto yield crystals
  3. filtrationThe crystals were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-88bef02453eb4624af3bc3568e27ac9f
Source dataset
uspto-grants-1987_08
Patent number
US04687777

Reaction notes

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