Hydrochloric Acid → Ciglitazone

HRID 326160Notes

Reaction equation

HRID 326160 reaction equation
CS(O[CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2([CH3:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=1)[C:7]([O:9]CC)=O)(=O)=O.[NH2:28][C:29](N)=[S:30].C([OH:34])C.Cl>O>[CH3:27][C:21]1([CH2:20][O:19][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][CH:6]3[S:30][C:29](=[O:34])[NH:28][C:7]3=[O:9])=[CH:18][CH:17]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2723790ThioureaHCID 20462534Ethyl 2-methanesulfonyloxy-3-[4-(1-methylcyclohexylmethyloxy)phenyl]propionate

Product 1

HCID 2750Ciglitazone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.0 g Of ethyl 2-methanesulfonyloxy-3-[4-(1-methylcyclohexylmethyloxy)phenyl]propionate and 760 mg. of thiourea are added to 20 ml of ethanol. The mixture is refluxed for 2 hours. To the mixture is added 10 ml of hydrochloric acid, and the mixture is further refluxed for 16 hours. After cooling, water is added to the mixture. The mixture is subjected to extraction with ethyl acetate. The extract is washed with water and dried. The ethyl acetate is distilled off to give 1.4 g of 5-[4-(1-methylcyclohexylmethyloxy)benzyl]thiazolidine-2,4-dione. Crystallization from 85% ethanol gives crystals melting at 130°-131° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. temperaturethe mixture is further refluxed for 16 hours
  3. temperatureAfter cooling
  4. extractionThe mixture is subjected to extraction with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. distillationThe ethyl acetate is distilled off

Sources & evidence

ORD record
ord-0af1828222bd4dcc908e91132b5180ad
Source dataset
uspto-grants-1984_04
Patent number
US04444779

Reaction notes

Loading…