Hydrochloric Acid → HCID 53970996, compound

HRID 429175Notes

Reaction equation

HRID 429175 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH2:6]([NH:13][C:14](=[O:25])[CH2:15][CH2:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.O>CO>[NH2:5][C:3]([NH:2][N:1]=[C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:16][CH2:15][C:14]([NH:13][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:25])=[S:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 347385N-benzyl-4-oxo-4-phenylbutanamideHCID 2723789Thiosemicarbazide

Product 1

HCID 53970996HCID 53970996, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide (2.30 g, 25.2 mmol) was added to a solution of N-benzyl-4-oxo-4-phenyl-butyramide (4.12 g, 15.4 mmol), prepared in the previous step, in 100 ml of methanol plus 4.2 ml of 1 N HCl plus 4.2 ml of water and the reaction stirred at room temperature for 20 hours. The reaction was cooled in an ice bath and a white solid precipitated. The solid was collected by filtration and dried to give 4.61 g of a white solid. Recrystallization of the solid from ethyl acetate-methanol gave the title compound (2.05 g, 39%) as a white solid, mp 162-164° C.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customa white solid precipitated
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-144b22ce3fc34e178458039d2f09b6db
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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