Hydrochloric Acid → HCID 9885141, compound

HRID 1380536Notes

Reaction equation

HRID 1380536 reaction equation
C([O:4][CH:5]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15](Br)[C:16]([O:18]C)=O)=[CH:10][CH:9]=1)(=O)C.[NH2:28][C:29](N)=[S:30].C([O-])(=[O:34])C.[Na+].Cl>C(O)C>[OH:4][CH:5]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=1)[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH:15]2[S:30][C:29](=[O:34])[NH:28][C:16]2=[O:18])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 13580523HCID 13580523, compound

Product 1

HCID 9885141HCID 9885141, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 3-{4-[2-acetoxy-2-(6-methyl-2-pyridyl)ethoxy]phenyl}-2-bromopropionate (3.2 g), thiourea (558 mg), sodium acetate (599 mg) and ethanol (30 ml) was heated under reflux for 4 hours, and then 6N-hydrochloric acid (30 ml) was added to the mixture, followed by heating under reflux for 16 hours. After neutralization with aqueous sodium hydrogencarbonate solution, the reaction mixture is extracted with chloroform, and the chloroform layer was washed with water and dried (MgSO4). After the solvent was distilled off, the residue was chromatographed on a silica-gel (100 g) column and elution was effected with benzene-acetone (10:1, V/V) to give 5-{4-[2-hydroxy-2-(6-methyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione in the form of crystals. Yield of 0.95 g. Recrystallization from ethyl acetate-hexane produced colorless prisms. m.p. 154°-155° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureby heating
  4. temperatureunder reflux for 16 hours
  5. extractionAfter neutralization with aqueous sodium hydrogencarbonate solution, the reaction mixture is extracted with chloroform
  6. washthe chloroform layer was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationAfter the solvent was distilled off
  9. customthe residue was chromatographed on a silica-gel (100 g) column and elution

Sources & evidence

ORD record
ord-42a4a0dd1b84493caef47fc3a841077f
Source dataset
uspto-grants-1986_04
Patent number
US04582839

Reaction notes

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