Hydrochloric Acid → HCID 14500684, compound

HRID 2350879Notes

Reaction equation

HRID 2350879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=S)[NH:10][NH2:11].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:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:22])[NH:11][N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 717704N-(2-Chlorophenyl)hydrazinecarbothioamide

Product 1

HCID 14500684HCID 14500684, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.05 g (0.05 mole) of 4-(2-chlorophenyl)-3-thiosemicarbazide in 75 mL of absolute ethanol was treated with 8.48 g (0.05 mole) of ethyl 2-choroacetoacetate and stirred under nitrogen atmosphere at room temperature for 1 hr. The reaction mixture was treated with 40 mL of 2N ethanolic hydrogen chloride and heated at reflux for 1 hr, during which time the yellow slurry became a clear, deep orange solution. The characteristic insoluble amorphous sulfur was removed by filtration. The filtrate began to solidify. It was allowed to cool for approximately 16 hr to yield 10.1 g of yellow crystalline product. The filtrate was concentrated in vacuo to yield an additional 3 g of yellow product. The 2 solids were combined and recrystallized from benzene to give 10.4 g of white crystalline product, mp 188°-189° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hr, during which time the yellow slurry
  3. customThe characteristic insoluble amorphous sulfur was removed by filtration
  4. temperatureto cool for approximately 16 hr

Sources & evidence

ORD record
ord-51847b17748142d68513e2afcf410544
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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