Hydrochloric Acid → HCID 14500678, compound

HRID 1761534Notes

Reaction equation

HRID 1761534 reaction equation
[C:1]1([NH:11][C:12](=S)[NH:13][NH2:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl[CH:17]([C:23]([CH3:25])=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19].Cl>C(O)C>[CH3:25][C:23]1[NH:14][N:13]=[C:12]([NH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 2760175N-(Naphthalen-1-yl)hydrazinecarbothioamide

Product 1

HCID 14500678HCID 14500678, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 15.0 g (0.069 mole) of 4-(1-naphthalenyl)-3-thiosemicarbazide and 11.4 g (0.069 mole) of ethyl 2-chloroacetoacetate in 100 mL of absolute ethanol was stirred at room temperature for 1 hr. Alcoholic hydrogen chloride (2N, 50 mL) was added, the mixture refluxed for 1 hr, filtered while hot and the filtrate evaporated under reduced pressure. The residue was recrystallized twice from 190 ethanol then twice from absolute ethanol to give 6.2 g of product, mp 199°-202° C. The sample was dried at 56° C./4 hr/0.1 mmHg then at 25° C./0.1 mmHg/for ~16 hr.

Workup

  1. temperaturethe mixture refluxed for 1 hr
  2. filtrationfiltered while hot and the filtrate
  3. customevaporated under reduced pressure
  4. customThe residue was recrystallized twice from 190 ethanol

Sources & evidence

ORD record
ord-2c09cf9326474e7aac9b5fb6876854ac
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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