Hydrochloric Acid → HCID 12798359, compound

HRID 2350886Notes

Reaction equation

HRID 2350886 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=S.Cl.[Cl:7][CH:8]([C:14]([CH3:16])=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[S]>C(O)C.O>[ClH:7].[NH2:5][C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:14]([CH3:16])[NH:1][N:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11858Ethyl 2-chloroacetoacetateHCID 2723789Thiosemicarbazide2×HCID 5362487Sulfur

Product 1

HCID 12798359HCID 12798359, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 9.1 g (0.1 mole) of 3-thiosemicarbazide and 1 mL of concentrated hydrochloride acid in 150 mL of absolute ethanol was cooled to 0° C. in an ice bath and 16.5 g (0.1 mole) of ethyl 2-chloroacetoacetate was added dropwise. The thiosemicarbazide dissolved as the reaction mixture was allowed to slowly come to ambient temperature, it then became yellow and a new precipitate formed. The reaction mixture was heated at reflux for 3 hr. All the material had not dissolved so the reaction mixture was diluted with water and made acidic with 3N hydrochloric acid to dissolve all the solids but sulfur. After filtering, the filtrate was concentrated in vacuo leaving an orange-red oil which slowly crystallized when acetone was added to give 11.5 g of orange powder, mp 186°-188° C., with decomposition.

Workup

  1. customto slowly come to ambient temperature
  2. customa new precipitate formed
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 3 hr
  5. dissolutionAll the material had not dissolved so the reaction mixture
  6. filtrationAfter filtering
  7. concentrationthe filtrate was concentrated in vacuo
  8. customleaving an orange-red oil which
  9. customslowly crystallized when acetone
  10. additionwas added

Sources & evidence

ORD record
ord-6fd0bcb87f1a42aa9e1f5cc35ba66ac4
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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