Hydrochloric Acid → HCID 54083650, compound

HRID 429170Notes

Reaction equation

HRID 429170 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH2:6]([NH:10][C:11](=[O:22])[CH2:12][CH2:13][C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH3:9].Cl.O>CO>[CH2:6]([NH:10][C:11](=[O:22])[CH2:12][CH2:13][C:14](=[N:1][NH:2][C:3]([NH2:5])=[S:4])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723789ThiosemicarbazideHCID 10728341HCID 10728341, compound

Product 1

HCID 54083650HCID 54083650, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide (1.95 g, 21.4 mmol) was added to a solution of N-butyl-4-oxo-4-phenyl-butyramide (5.0 g, 21.4 mmol), prepared in the previous step, in 75 ml of methanol plus 5.8 ml of 1 N HCl plus 5.8 ml of water and the reaction stirred at room temperature for 22 hours. The reaction was concentrated under reduced pressure at which time a solid formed. The solid was collected by filtration and dried to give 4.49 g of an off-white solid. Recrystallization of the solid from isopropyl alcohol gave 3.16 g (48%) of the title compound as a white solid, mp 64-68° C.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure at which time a solid
  2. customformed
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-69a0f926d1e44c14940dcc76e168d41d
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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