Sodium Bicarbonate → 2-Imino-5-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3-pyridinyl]-1,3-thiazolidin-4-one

HRID 2395698Notes

Reaction equation

HRID 2395698 reaction equation
COC(=O)[CH:4](Br)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[N:10][CH:11]=1.[NH2:29][C:30]([NH2:32])=[S:31].C([O-])(=[O:35])C.[Na+].C([O-])(O)=O.[Na+]>CCOCC.C(O)C>[NH:29]=[C:30]1[NH:32][C:4](=[O:35])[CH:5]([C:6]2[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][C:15]3[N:16]=[C:17]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[O:18][C:19]=3[CH3:20])=[N:10][CH:11]=2)[S:31]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 536876832-Bromo-3-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]propionic acid methyl ester

Product 1

HCID 1532758862-Imino-5-[6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3-pyridinyl]-1,3-thiazolidin-4-oneYield 90.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-bromo-3-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]propionic acid methyl ester (1.07 g), thiourea (0.2 g), sodium acetate (0.22 g) and ethanol (25 ml) was heated for 2.5 hours while refluxing. To the reaction mixture was added a saturated aqueous solution of NaHCO3 and ether, and the resulting crystal was collected by filtration, to yield 2-imino-5-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]-4-thiazolidinone (0.86 g, 88%) (recrystallized from chloroform-methanol) as a colorless crystal.

Workup

  1. temperaturewas heated for 2.5 hours
  2. temperaturewhile refluxing
  3. filtrationthe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-d5606a59d74d486a96f50ccdd20a40b4
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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