Hydrochloric Acid → HCID 86749241, compound

HRID 2395692Notes

Reaction equation

HRID 2395692 reaction equation
CO[C:3](=[O:28])[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)[S:18][C:19]=2[CH3:20])=[N:10][CH:11]=1.[NH2:29][C:30](N)=[S:31].C([OH:35])C.Cl>O>[CH3:20][C:19]1[S:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:16][C:15]=1[CH2:14][CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH:4]2[S:31][C:30](=[O:35])[NH:29][C:3]2=[O:28])=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2723790ThioureaHCID 54179568HCID 54179568, compound

Product 1

HCID 86749241HCID 86749241, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromo-3-[2-[2-(5-methyl-2-phenyl-4-thiazolyl)ethoxy]-5-pyridyl]propionic acid methyl ester (1.40 g), thiourea (0.25 g) and ethanol (20 ml) was heated for 4.5 hours while refluxing, followed by addition of 2N hydrochloric acid (20 ml) and heating for 18 more hours under refluxing conditions. The reaction mixture was added to water and extracted with dichloromethane. After the dichloromethane layer was washed with water and dried (MgSO4), the solvent was distilled off. The residual crystal was recrystallized from ethanol-chloroform to yield 5-[[2-[2-(5-methyl-2-phenyl-4-thiazolyl)ethoxy]-5-pyridyl]methyl]-2,4-thiazolidinedione (0.66 g, 51%) as a colorless crystal.

Workup

  1. temperaturewas heated for 4.5 hours
  2. temperaturewhile refluxing
  3. temperatureheating for 18 more hours under refluxing conditions
  4. extractionextracted with dichloromethane
  5. washAfter the dichloromethane layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationthe solvent was distilled off
  8. customThe residual crystal was recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-706434453ba84123a84ab2a0db9d64e3
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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