Hydrochloric Acid → 4-[(Aminothioxomethyl)-hydrazono]-4-phenylbutanamide

HRID 429173Notes

Reaction equation

HRID 429173 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].O=[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][CH2:9][C:10]([NH2:12])=[O:11].Cl.O>CO>[NH2:5][C:3]([NH:2][N:1]=[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[S:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5200224-Oxo-4-phenylbutanamideHCID 2723789Thiosemicarbazide

Product 1

HCID 538040944-[(Aminothioxomethyl)-hydrazono]-4-phenylbutanamideYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide (1.38 g, 15.1 mmol) was added to a solution of 4-oxo-4-phenyl-butyramide (1.63 g, 9.22 mmol), prepared in the previous step, in 50 ml of methanol plus 2.5 ml of 1 N HCl plus 2.5 ml of water and the reaction stirred at room temperature for 28 hours. The solid formed was collected by filtration and dried to give 1.73 g of a purple solid. Recrystallization of the solid from methanol gave the title compound (1.34 g, 58%) as a purple solid, mp 186-188° C.

Workup

  1. customThe solid formed
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-30aeca9f6a5745588b90d299c38e546f
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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