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Hydrochloric Acid → Phenyl-3-thiosemicarbazonopropionic acid ethyl ester (thiosemicarbazone)

HRID 2263582
Notes
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Reaction equation

HRID 2263582 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[S:5].[C:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=O)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>CO>[N:2](=[C:16]([O:18][CH2:19][CH3:20])[C:15](=[N:2][NH:3][C:4]([NH2:6])=[S:5])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:3][C:4]([NH2:6])=[S:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7170Ethyl benzoylacetateHCID 3037943Thiosemicarbazide Hydrochloride

Product 1

HCID 86613479Phenyl-3-thiosemicarbazonopropionic acid ethyl ester (thiosemicarbazone)Yield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide hydrochloride (8.30 g, 65.1 mmol) was dissolved in a mixed solvent of methanol (50 mL) and distilled water (50 mL). To the solution was added ethyl benzoylacetate (17.0 mL, 98.2 mmol) and concentrated hydrochloric acid (1.00 mL, 12.0 mmol), and the mixture was stirred at room temperature for 11 hours. The deposited solid was collected by filtration, washed (methanol) and then dried to give 3 phenyl-3-thiosemicarbazonopropionic acid ethyl ester (thiosemicarbazone) (11.1 g, 64%).

Workup

  1. distillationdistilled water (50 mL)
  2. filtrationThe deposited solid was collected by filtration
  3. washwashed (methanol)
  4. customdried

Sources & evidence

ORD record
ord-36cd28126f0d42ae9e5bf7c513f26e7b
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851635B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes