Hydrochloric Acid → 5-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

HRID 1901191Notes

Reaction equation

HRID 1901191 reaction equation
Cl[CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17](=[O:19])[CH3:18])=[CH:11][CH:10]=1)[C:3]([O:5]CC)=O.[NH2:20][C:21](N)=[S:22].S1(CCCC1)(=O)=[O:25].COC(O)C.Cl>C(OCC)(=O)C.O>[O:19]=[C:17]([CH3:18])[CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:2]2[S:22][C:21](=[O:25])[NH:20][C:3]2=[O:5])=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 30156371-MethoxyethanolHCID 21832172HCID 21832172, compound

Product 1

HCID 218321505-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture comprising 12 g of ethyl 2-chloro-3-[4-(2-oxopropoxy)phenyl]propionate [prepared as described in step (b) above], 5 g of thiourea and 30 ml of sulfolane was heated at 90° C. for 3 hours, and then 100 ml of methoxyethanol were added to the mixture, which was then heated for a further 4 hours. At the end of this time, 40 ml of water and 20 ml of concentrated aqueous hydrochloric acid were added to the reaction mixture, and the resulting mixture was heated for 4.5 hours in an oil bath kept at 100° C. After this, the reaction mixture was mixed with water and ethyl acetate, and then the ethyl acetate layer was separated, washed with water and dried over anhydrous sodium sulfate; the solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 3:2 to 2:3 by volume as the eluent, followed by crystallization from a mixture of ethyl acetate and hexane, to give the title compound as crystals, melting at 158°-159° C.

Workup

  1. temperaturewas then heated for a further 4 hours
  2. temperaturethe resulting mixture was heated for 4.5 hours in an oil bath
  3. customkept at 100° C
  4. customthe ethyl acetate layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was then removed by distillation under reduced pressure
  8. customThe resulting residue was purified by column chromatography through silica gel
  9. washa gradient elution method
  10. customwith mixtures of hexane and ethyl acetate ranging from 3:2 to 2:3 by volume as the eluent, followed by crystallization from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-4a1567264a984f8986a4ced3ba6f7cdc
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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