Ethyl 2-chloroacetoacetate → HCID 14500711, compound

HRID 1761552Notes

Reaction equation

HRID 1761552 reaction equation
[CH:1]1([NH:6][C:7](=S)[NH:8][NH2:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:11][CH:12]([C:18]([CH3:20])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[ClH:11].[CH:1]1([NH:6][C:7]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]([CH3:20])[NH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 2037202HCID 2037202, compound

Product 1

HCID 14500711HCID 14500711, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred slurry of 8.3 g (0.052 mole) of 4-cyclopentyl-3-thiosemicarbazide in 50 mL of absolute ethanol under nitrogen atmosphere was treated with 8.6 g (0.052 mole) of ethyl 2-chloroacetoacetate. The reaction mixture which, after filtering, turned pale yellow, was stirred for 18 hr at ambient temperature, treated with 20 mL of 2N ethanolic hydrogen chloride and heated at reflux for 1 hr. The reaction mixture was filtered hot and the filtrate concentrated in vacuo to a yellow-orange solid. Most of the solid was dissolved in 100 mL of hot absolute ethanol. The mixture was filtered, and when the filtrate was treated with dipropyl ether (150 mL) a precipitate formed which was collected by filtration to give 11.7 g of crude product. Recrystallization from benzene/ligroin with charcoal treatment gave 7.6 g of fine white fluffy needles, mp 175°-177° C.

Workup

  1. filtrationThe reaction mixture which, after filtering
  2. additiontreated with 20 mL of 2N ethanolic hydrogen chloride
  3. temperatureheated
  4. temperatureat reflux for 1 hr
  5. filtrationThe reaction mixture was filtered hot
  6. concentrationthe filtrate concentrated in vacuo to a yellow-orange solid
  7. dissolutionMost of the solid was dissolved in 100 mL of hot absolute ethanol
  8. filtrationThe mixture was filtered
  9. additionwhen the filtrate was treated with dipropyl ether (150 mL) a precipitate
  10. customformed which
  11. filtrationwas collected by filtration
  12. customto give 11.7 g of crude product
  13. customRecrystallization from benzene/ligroin with charcoal treatment

Sources & evidence

ORD record
ord-e97c752362ca49aaad8156758ed054fa
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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