Hydrochloric Acid → Troglitazone

HRID 1030369Notes

Reaction equation

HRID 1030369 reaction equation
C([O:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27](Cl)[C:28](OCC)=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2)(=O)C.[NH2:35][C:36](N)=[S:37].S1(CCCC1)(=O)=[O:40].Cl>COCCO>[OH:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]3[S:37][C:36](=[O:40])[NH:35][C:28]3=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 13605832HCID 13605832, compound

Product 1

HCID 5591Troglitazone

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 9.6 g of ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate (prepared as described in Preparation 51), 1.8 g of thiourea and 11 ml of sulfolane was heated for 3.5 hours at 120° C. under a nitrogen stream. 100 ml of ethylene glycol monomethyl ether and 70 ml of 10% w/v aqueous hydrochloric acid were then added to the reaction mixture, after which it was heated under reflux for 12 hours. The product was then purified as described in Example 27, to give the title compound. The melting point and nuclear magnetic resonance spectrum of this compound accorded with those of the compound obtained in Example 27(b).

Workup

  1. additionwere then added to the reaction mixture
  2. temperatureafter which it was heated
  3. temperatureunder reflux for 12 hours
  4. customThe product was then purified

Sources & evidence

ORD record
ord-1921ecf4562841c598ff796274bf7166
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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