Hydrochloric Acid → HCID 14500698, compound

HRID 2350883Notes

Reaction equation

HRID 2350883 reaction equation
[CH2:1]([NH:4][C:5](=S)[NH:6][NH2:7])[CH:2]=[CH2:3].[Cl:9][CH:10]([C:16]([CH3:18])=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>C(O)C>[ClH:9].[CH3:18][C:16]1[NH:7][N:6]=[C:5]([NH:4][CH2:1][CH:2]=[CH2:3])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 1551250Hydrazinecarbothioamide, N-2-propenyl- (9CI)

Product 1

HCID 14500698HCID 14500698, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 26.24 g (0.2 mole) of 4-(2-propenyl)-3-thiosemicarbazide and 32.9 g (0.2 mole) of ethyl 2-chloroacetoacetate in 150 mL of absolute ethanol was stirred under nitrogen atmosphere for 1.5 hr, treated with 100 mL of 2N ethanolic hydrogen chloride and heated at reflux for 1.5 hr. The reaction mixture was stirred at ambient temperature for ~72 hr, heated to reflux and filtered to remove the amorphous sulfur. The filtrate was concentrated in vacuo to give a deep red oil which crystallized on trituration with acetone to give 29 g of product. Recrystallization from acetone gave 21 g of needle-like crystals tinted with yellow. A second recrystallization from benzene gave 15.8 g of fine white needles, mp 133°-134° C. A rework of the filtrates from both recrystallizations gave an additional 7 g of crude product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hr
  3. stirringThe reaction mixture was stirred at ambient temperature for ~72 hr
  4. temperatureheated
  5. temperatureto reflux
  6. filtrationfiltered
  7. customto remove the amorphous sulfur
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give a deep red oil which
  10. customcrystallized on trituration with acetone

Sources & evidence

ORD record
ord-0fdd508976f74c66b29d7f441c7374a4
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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