Hydrochloric Acid → HCID 14500677, compound

HRID 1761533Notes

Reaction equation

HRID 1761533 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=S)[NH:11][NH2:12])[CH:6]=[CH:7][CH:8]=1.Cl[CH:15]([C:21]([CH3:23])=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>C(O)C>[CH3:23][C:21]1[NH:12][N:11]=[C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([S:2][CH3:1])[CH:4]=2)[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 27600984-[3-(Methylthio)phenyl]-3-thiosemicarbazide

Product 1

HCID 14500677HCID 14500677, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 10.0 g (0.046 mole) of 4-(3-methylthiophenyl)-3-thiosemicarbazide and 7.72 g (0.0469 mole) of ethyl 2-chloroacetoacetate in 150 mL of absolute ethanol was stirred at room temperature for ~16 hr. Ethanolic hydrogen chloride (2N, 50 mL) was added, the mixture refluxed for 1.0 hr, the solution filtered while hot, and the filtrate evaporated under reduced pressure to give a crystalline residue which was recrystallized three times from absolute ethanol to give 6.3 g product, mp 191.5°-194° C. The sample was dried at 56° C./4 hr/0.1 mmHg then 2 hr/25° C./0.1 mmHg.

Workup

  1. temperaturethe mixture refluxed for 1.0 hr
  2. filtrationthe solution filtered while hot, and the filtrate
  3. customevaporated under reduced pressure
  4. customto give a crystalline residue which
  5. customwas recrystallized three times from absolute ethanol

Sources & evidence

ORD record
ord-bbdd37ac277c42e8870751f3c05dcd51
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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