Hydrochloric Acid → HCID 11004363, compound

HRID 1739016Notes

Reaction equation

HRID 1739016 reaction equation
Cl[CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)[C:3](OCC)=[O:4].[NH2:31][C:32](N)=[S:33].C([O-])(=[O:37])C.[Na+].Cl>O.C(O)C>[CH3:24][C:23]1[O:22][C:21]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:20][C:19]=1[CH2:18][CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH:2]2[S:33][C:32](=[O:37])[NH:31][C:3]2=[O:4])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 10873631HCID 10873631, compound

Product 1

HCID 11004363HCID 11004363, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 2-chloro-4-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butyrate (0.20 g), thiourea (0.145 g), sodium acetate (0.115 g) and ethanol (15 ml) was heated under reflux for 30 hours. 6N hydrochloric acid (15 ml) was added, and the mixture was heated under reflux for 15 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with methanol-chloroform (2:98, v/v) gave 5-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]ethyl]-2,4-thiazolidinedione (0.11 g, 56%). This product was recrystallized from dichloromethane-ethanol. Colorless prisms, mp: 151-152° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 15 hours
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated
  9. washThe fractions eluted with methanol-chloroform (2:98

Sources & evidence

ORD record
ord-a99232567e884950916a9792c6e6049a
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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