Hydrochloric Acid → HCID 72644370, compound

HRID 1581643Notes

Reaction equation

HRID 1581643 reaction equation
[CH3:1][S:2][CH:3]([C:9]1[CH:14]=[C:13]([CH:15]=O)[CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[S:19]1[CH2:23][C:22](=[O:24])[NH:21][C:20]1=[O:25].N1CCCCC1.Cl>C(O)C>[CH3:1][S:2][CH:3]([C:9]1[CH:14]=[C:13]([CH:15]=[C:23]2[S:19][C:20](=[O:25])[NH:21][C:22]2=[O:24])[CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 10934463HCID 10934463, compound

Product 1

HCID 72644370HCID 72644370, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-methylthio-2-(5-formyl-2-methoxyphenyl)acetate (7.50 g, 28.0 mmol), thiazolidine-2,4-dione (3.94 g, 33.6 mmol), piperidine (2.80 mL, 28.3 mmol) and ethanol (100 mL) were mixed and refluxed for 14 hours. After allowed to stand for cooling, concentrated hydrochloric acid was added under cooling with ice and stirring to make the reaction mixture acidic. Ice water was added thereto and the mixture was stirred for 30 minutes. The precipitated crystals were collected by filtration, washed with ethanol and water, and then dried to obtain 6.18 g (60%) of the title compound as yellow crystals.

Workup

  1. temperaturerefluxed for 14 hours
  2. temperaturefor cooling
  3. temperatureunder cooling with ice
  4. stirringthe mixture was stirred for 30 minutes
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with ethanol and water
  7. customdried

Sources & evidence

ORD record
ord-a6c9ec45c236429982e69db2e0874b8f
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

Loading…