Hydrochloric Acid → HCID 13580526, compound

HRID 1380540Notes

Reaction equation

HRID 1380540 reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][N:20]=2)[CH2:17][OH:18])=[CH:10][CH:9]=1)[C:3]([O:5]C)=O.[NH2:27][C:28](N)=[S:29].C([O-])(=[O:33])C.[Na+].Cl>C(O)C>[CH2:25]([C:22]1[CH:23]=[CH:24][C:19]([CH:16]([CH2:17][OH:18])[CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH:2]3[S:29][C:28](=[O:33])[NH:27][C:3]3=[O:5])=[CH:9][CH:10]=2)=[N:20][CH:21]=1)[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 14546502HCID 14546502, compound

Product 1

HCID 13580526HCID 13580526, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 2-bromo-3-{4-[2-(5-ethyl-2-pyridyl)-3-hydroxypropoxy]phenyl}propionate (12.2 g), thiourea (2.2 g), sodium acetate (2.4 g) and ethanol (100 ml) was heated under reflux for 3 hours, and 3N-hydrochloric acid (100 ml) was added to the mixture, followed by heating under reflux for 12 hours. After concentration, the reaction mixture was neutralized with aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then freed of the solvent. The residue was chromatographed on a silica-gel (200 g) column, and elution was effected with benzene-acetone (5:1, V/V) to give 5-{4-[2-(5-ethyl-2-pyridyl)-3-hydroxypropoxy]benzyl}-2,4-thiazolidinedione in the form of an oily substance. Yield of 4.8 g (42.9%). The substance was dissolved in methanol (15 ml), and sodium methylate (28% methanol solution, 2.9 g) was added to the solution, followed by addition of ethyl ether (150 ml) to give the sodium salt in the form of crystals. Yield of 4.8 g (40.7%). Recrystallization from ethanol-ethyl ether produced colorless prisms. m.p. 237°-238° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureby heating
  4. temperatureunder reflux for 12 hours
  5. concentrationAfter concentration
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. dry with materialdried (MgSO4)
  9. customThe residue was chromatographed on a silica-gel (200 g) column, and elution

Sources & evidence

ORD record
ord-80988af9bb5b4a338291033694bb0b1d
Source dataset
uspto-grants-1986_04
Patent number
US04582839

Reaction notes

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