Hydrochloric Acid → AD-5061

HRID 4388Notes

Reaction equation

HRID 4388 reaction equation
N=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][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])=[CH:11][CH:10]=2)[S:3]1.Cl.C([OH:33])C>>[CH3:23][C:22]1[O:21][C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=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][CH:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1532755332-Imino-5-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,3-thiazolidin-4-one

Product 1

HCID 9953271AD-5061Yield 95.7%

Procedure

A mixture of 2-imino-5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-4-thiazolidinone (18.8 g), 2N-HCl (200 ml) and ethanol (200 ml) was heated under reflux for 12 hours. The solvent was distilled off under reduced pressure. The residue was neutralized with saturated aqueous solution of sodium hydrogen carbonate, and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4). The solvent was distilled off, whereby 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione (18.0 g, 95.7%) was obtained. Recrystallization from ethanol afforded colorless needles. m.p. 113°-114° C. Elemental Analysis for C22H20N2O4S, Calcd.: C, 64.69; H, 4.93; N, 6.86. Found: C, 64.48; H, 4.91; N, 6.75.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-8b455a0376424e3e96c5ad5aa252a94c
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Reaction notes

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