Hydrochloric Acid → HCID 9844388, compound

HRID 2395691Notes

Reaction equation

HRID 2395691 reaction equation
N=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][C:18]3[N:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:21][C:22]=3[CH3:23])=[N:13][CH:14]=2)[S:3]1.Cl.C([OH:33])C>>[CH3:23][C:22]1[O:21][C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:19][C:18]=1[CH2:17][CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:4]2[S:3][C:2](=[O:33])[NH:6][C:5]2=[O:7])=[CH:14][N:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 145824090HCID 145824090, compound

Product 1

HCID 9844388HCID 9844388, compoundYield 59%

Procedure

A mixture of 2-imino-5-[[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]methyl]-4-thiazolidinone (0.76 g), 1N HCl (10 ml) and ethanol (10 ml) was heated for 20 hours while refluxing, followed by concentration under reduced pressure. The residual crystal was collected by filtration, washed with water and then recrystallized from ethanol-chloroform to yield 5-[[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]methyl]-2,4-thiazolidinedione (0.45 g, 59%) as a colorless crystal.

Workup

  1. temperaturewas heated for 20 hours
  2. temperaturewhile refluxing
  3. concentrationfollowed by concentration under reduced pressure
  4. filtrationThe residual crystal was collected by filtration
  5. washwashed with water
  6. customrecrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-adef120bb22c4b17aa30af85b941d7bc
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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