Ethyl 2-chloroacetoacetate → HCID 19965125, compound

HRID 977090Notes

Reaction equation

HRID 977090 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([NH2:10])=[S:9])([CH3:3])[CH3:2].Cl[CH:15]([C:21]([CH3:23])=O)[C:16]([O:18]CC)=[O:17]>C(O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:8]2[S:9][C:15]([C:16]([OH:18])=[O:17])=[C:21]([CH3:23])[N:10]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 19965069HCID 19965069, compound

Product 1

HCID 19965125HCID 19965125, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

390 mg of 3-Isopropoxythiobenzamide was dissolved in 5 ml of ethanol, 360 mg of ethyl 2-chloroacetoacetate was added to the solution, and the mixture was heated under reflux for five hours. After the reaction mixture was cooled, it was concentrated and subjected to silica gel chromatography (eluent, hexane: ethyl acetate=9:1) to separate an intended product (490 mg). The resulting oily substance was dissolved in 5 ml of ethanol, 10 ml of a 1N aqueous sodium hydroxide solution was added, and the mixture was heated at 70° C. for one hour. After the completion of the reaction, ethanol was removed by distillation and the residue was neutralized with 1N hydrochloric acid. The precipitated crystal was collected by filtration and recrystallized from a 50% aqueous ethanol solution to give 358 mg of 2-(3-isopropoxyphenyl)-4-methyl-5-thiazolecarboxylic acid (yield: 65%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for five hours
  3. temperatureAfter the reaction mixture was cooled
  4. concentrationit was concentrated
  5. customto separate an intended product (490 mg)
  6. dissolutionThe resulting oily substance was dissolved in 5 ml of ethanol
  7. addition10 ml of a 1N aqueous sodium hydroxide solution was added
  8. customAfter the completion of the reaction, ethanol
  9. customwas removed by distillation
  10. filtrationThe precipitated crystal was collected by filtration
  11. customrecrystallized from a 50% aqueous ethanol solution

Sources & evidence

ORD record
ord-d627428acbb441d387cbfe41b42af560
Source dataset
uspto-grants-1997_03
Patent number
US05614520

Reaction notes

Loading…