Hydrochloric Acid → 5-[4-(2,4,5-Trimethyl-3,6-dimethoxyphenoxy)benzyl]thiazolidine-2,4-dione

HRID 1742485Notes

Reaction equation

HRID 1742485 reaction equation
Br[CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:23]([O:24][CH3:25])=[C:22]([CH3:26])[C:21]([CH3:27])=[C:20]([O:28][CH3:29])[C:19]=2[CH3:30])=[CH:13][CH:12]=1)[C:3](OCCCC)=[O:4].[NH2:31][C:32](N)=[S:33].S1(CCCC1)(=O)=[O:36].Cl>O.COCCO>[CH3:30][C:19]1[C:20]([O:28][CH3:29])=[C:21]([CH3:27])[C:22]([CH3:26])=[C:23]([O:24][CH3:25])[C:18]=1[O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH:2]2[S:33][C:32](=[O:36])[NH:31][C:3]2=[O:4])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 19009256Butyl 2-bromo-3-[4-(2,4,5-trimethyl-3,6-dimethoxyphenoxy)phenyl]propionate

Product 1

HCID 190092435-[4-(2,4,5-Trimethyl-3,6-dimethoxyphenoxy)benzyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5.7 g of butyl 2-bromo-3-[4-(2,4,5-trimethyl-3,6-dimethoxyphenoxy)phenyl]propionate (prepared as described in Preparation 1), 1.2 g of thiourea and 10 ml of sulfolane was heated at 120° C. for 5 hours under an atmosphere of nitrogen, and then 20 ml of ethylene glycol monomethyl ether and 10 ml of 2N aqueous hydrochloric acid were added to the resulting mixture. The mixture was then heated at 100° C. for 5 hours, after which the reaction mixture was poured into water and then extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed from the extract by distillation under reduced pressure, and the residue thus obtained was purified by column chromatography through silica gel, using a 9:1 by volume mixture of benzene and ethyl acetate as the eluent, to give 4.7 g of the title compound as a white glassy powder softening at 47°-50° C.

Workup

  1. temperatureThe mixture was then heated at 100° C. for 5 hours
  2. extractionextracted with benzene
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed from the
  6. extractionextract by distillation under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by column chromatography through silica gel
  9. additionby volume mixture of benzene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-233d4c63612a4407af066987dd27d807
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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