Ethyl 4-chloroacetoacetate → HCID 22282979, compound

HRID 1919570Notes

Reaction equation

HRID 1919570 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7]CC)=O.[CH:11]([NH2:13])=[S:12].O.[NH3:15]>C(O)C>[CH3:2][C:3]1[N:13]=[CH:11][S:12][C:4]=1[C:5]([NH2:15])=[O:7]

Participants

5

Reactant 3

HCID 69484Ethyl 4-chloroacetoacetateHCID 3005587MethanethioamideHCID 12896473Azane;hydrate

Product 1

HCID 22282979HCID 22282979, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.3 g (20 mmol) ethyl chloroacetoacetate and 1.8 g (30 mmol) thioformamide were dissolved in 40 ml ethanol, and reacted under reflux for 8 hr, followed by removing the solvent by rotation drying; and then, ethyl acetate and water were added to separate the layers. The resultant organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a red oily liquid. 60 ml ammonia water was directly added to the red oily liquid without purification, to carry out reaction in closed state for 24 hr. The reaction product was extracted with ethyl acetate, dried with sodium sulfate, filtered and concentrated to obtain 2.3 g of a solid (yield 82%).

Workup

  1. customreacted
  2. temperatureunder reflux for 8 hr
  3. customby removing the solvent by rotation
  4. customdrying
  5. additionand then, ethyl acetate and water were added
  6. customto separate the layers
  7. dry with materialThe resultant organic phase was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto obtain a red oily liquid
  11. customreaction in closed state for 24 hr
  12. extractionThe reaction product was extracted with ethyl acetate
  13. dry with materialdried with sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-fe2f9940ef86491abd9be178b2aace6f
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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