Sodium Bicarbonate → HCID 140341974, compound

HRID 1380537Notes

Reaction equation

HRID 1380537 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[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:17][OH:18])=[CH:10][CH:9]=1)[C:3](OC)=[O:4].[NH2:26][C:27]([NH2:29])=[S:28].C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>O.C(O)C>[OH:18][CH2:17][CH:16]([C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=1)[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH:2]2[S:28][C:27](=[NH:26])[NH:29][C:3]2=[O:4])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 14546504HCID 14546504, compound

Product 1

HCID 140341974HCID 140341974, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-bromo-3-{4-[3-hydroxy-2-(3-methyl-2-pyridyl)propoxy]phenyl}propionate (4.7 g), thiourea (875 mg), sodium acetate (943 mg) and ethanol (50 ml) was heated under reflux for 3 hours. The mixture was diluted with water, neutralized with aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and freed of the solvent to give 5-{4-[3-hydroxy-2-(3-methyl-2-pyridyl)propoxy]-benzyl}-2-imino-4-thiazolidinone in the form of crystals. Yield of 25 g. Recrystallization from chloroform-methanol produced colorless prisms. m.p. 213°-214° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-81fb877ddb424c7fa3a9168e51cf8620
Source dataset
uspto-grants-1986_04
Patent number
US04582839

Reaction notes

Loading…