Ethyl 2-chloroacetoacetate → HCID 14500700, compound

HRID 1761544Notes

Reaction equation

HRID 1761544 reaction equation
[CH2:1]([NH:3][C:4](=S)[NH:5][NH2:6])[CH3:2].[Cl:8][CH:9]([C:15]([CH3:17])=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11]>Cl>[ClH:8].[CH2:1]([NH:3][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:15]([CH3:17])[NH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 15517804-Ethyl-3-thiosemicarbazide

Product 1

HCID 14500700HCID 14500700, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 47.68 g (0.4 mole) of 4-ethyl-3-thiosemicarbazide and 65.8 g (0.4 mole) of ethyl 2-chloroacetoacetate was stirred under nitrogen atmosphere for 1.5 hr at ambient temperature then treated with 200 mL of 2N ethanolic hydrogen chloride. The mixture was stirred for ~72 hr, filtered to remove the amorphous sulfur, and the solvent was removed in vacuo to give a deep amber oil which solidified. Recrystallization from acetone gave 27 g of crude product which was recrystallized from benzene/petroleum ether to give 23.5 g of fine white crystals, mp 140°-148° C. Rework of the filtrate gave an additional 17.5 g of crude product.

Workup

  1. stirringThe mixture was stirred for ~72 hr
  2. filtrationfiltered
  3. customto remove the amorphous sulfur
  4. customthe solvent was removed in vacuo
  5. customto give a deep amber oil which
  6. customRecrystallization from acetone
  7. customgave 27 g of crude product which
  8. customwas recrystallized from benzene/petroleum ether

Sources & evidence

ORD record
ord-30b5be4e643f4d99838273a12271a051
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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