Hydrochloric Acid → HCID 14500720, compound

HRID 2350895Notes

Reaction equation

HRID 2350895 reaction equation
[CH2:1]([NH:7][C:8](=S)[NH:9][NH2:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl:12][CH:13]([C:19]([CH3:21])=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>C(O)C>[ClH:12].[CH2:1]([NH:7][C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:19]([CH3:21])[NH:10][N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 27592834-Hexyl-3-thiosemicarbazide

Product 1

HCID 14500720HCID 14500720, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 15.8 g (0.091 mole) of 4-hexyl-3-thiosemicarbazide in 150 mL of absolute ethanol under nitrogen atmosphere was treated with 14.8 g (0.091 mole) of ethyl 2-chloroacetoacetate, stirred for 2.5 hr at ambient temperature, treated with 50 mL of 2N ethanolic hydrogen chloride, heated at reflux for 1 hr, and stirred at ambient temperature ~16 hr. The reaction mixture was heated to dissolve most of the solids, filtered to remove the insoluble sulfur and concentrated in vacuo to give a deep red-orange oil. After standing for 3 weeks at ambient temperature, the oil began to crystallize. Trituration with ethyl acetate and filtration gave 13 g of crude product, which was recrystallized from acetone/diethyl ether to give 7.5 g of white granular product, mp 108°-109° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. stirringstirred at ambient temperature ~16 hr
  4. temperatureThe reaction mixture was heated
  5. dissolutionto dissolve most of the solids
  6. filtrationfiltered
  7. customto remove the insoluble sulfur
  8. concentrationconcentrated in vacuo
  9. customto give a deep red-orange oil
  10. waitAfter standing for 3 weeks at ambient temperature
  11. customto crystallize
  12. filtrationTrituration with ethyl acetate and filtration
  13. customgave 13 g of crude product, which
  14. customwas recrystallized from acetone/diethyl ether

Sources & evidence

ORD record
ord-892fbfb8fb984c8da2da64c329582e3a
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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