Ethanol → HCID 13580524, compound

HRID 1380538Notes

Reaction equation

HRID 1380538 reaction equation
[OH:1][CH2:2][CH:3]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=1)[CH2:4][O:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][CH:11]2[S:15][C:14](=N)[NH:13][C:12]2=[O:17])=[CH:8][CH:7]=1.C([OH:29])C>Cl>[OH:1][CH2:2][CH:3]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=1)[CH2:4][O:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][CH:11]2[S:15][C:14](=[O:29])[NH:13][C:12]2=[O:17])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 140341974HCID 140341974, compound

Product 1

HCID 13580524HCID 13580524, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-{4-[3-hydroxy-2-(3-methyl-2-pyridyl)propoxy]benzyl}-2-imino-4-thiazolidinone (2.3 g) was dissolved in a mixture of 2N-hydrochloric acid and ethanol (20 ml), and the solution was heated under reflux for 4 hours. After neutralization with aqueous sodium hydrogencarbonate solution, the solution was extracted with chloroform, and the chloroform layer was washed with water and dried (MgSO4). The solvent was distilled off to give 5-{4-[3-hydroxy-2-(3-methyl-2-pyridyl)propoxy]-benzyl}-2,4-thiazolidinedione in the form of crystals. Yield of 1.9 g. Recrystallization from ethanol produced colorless prisms. m.p. 182°-183° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 4 hours
  3. extractionAfter neutralization with aqueous sodium hydrogencarbonate solution, the solution was extracted with chloroform
  4. washthe chloroform layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a2052add639948c58b5fa55c1bb07867
Source dataset
uspto-grants-1986_04
Patent number
US04582839

Reaction notes

Loading…