Hydrochloric Acid → HCID 14500687, compound

HRID 1761540Notes

Reaction equation

HRID 1761540 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=S)[NH:10][NH2:11])[CH:5]=[CH:6][CH:7]=1.Cl[CH:14]([C:20]([CH3:22])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:22])[NH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 707050N-(3-Chlorophenyl)hydrazinecarboximidothioic acid

Product 1

HCID 14500687HCID 14500687, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred slurry of 8 g (0.04 mole) of 4-(3-chlorophenyl)-3-thiosemicarbazide in 75 mL of absolute ethanol was treated with 6.8 g (0.04 mole) of ethyl 2-chloroacetoacetate. The reactants quickly dissolved but a precipitate soon formed. After stirring at room temperature for 2 hr the reaction mixture was treated with 40 mL of 2N ethanolic hydrogen chloride and heated at reflux for 1 hr, then filtered while hot to remove the insoluble sulfur. The filtrate on cooling yielded 3.5 g of yellow solid and an additional 4.7 g was obtained when the filtrate was concentrated in vacuo. Recrystallization from benzene/ligroin gave 4.2 g of pale yellow brown product. Additional ligroin added to the filtrate gave, upon cooling at ~7°-10° C. for ~16 hr, additional crystals but also some oil; this tri-phase mixture was filtered to yield 1.5 g of additional product. Both solids had identical spectra. They were combined and recrystallized twice from benzene/ligroin and finally from benzene by dissolving the solids and reducing the volume until crystallization began. Upon cooling, 3.93 g of beige plate-like crystals were collected, mp 159.5°-160° C.

Workup

  1. dissolutionThe reactants quickly dissolved
  2. customa precipitate soon formed
  3. temperatureheated
  4. temperatureat reflux for 1 hr
  5. filtrationfiltered while hot
  6. customto remove the insoluble sulfur
  7. temperatureThe filtrate on cooling

Sources & evidence

ORD record
ord-c104a35038c549c38bb949113b654f9d
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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