Hydrochloric Acid → HCID 53966896, compound

HRID 429171Notes

Reaction equation

HRID 429171 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH3:6][CH:7]([NH:9][C:10](=[O:21])[CH2:11][CH2:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:8].Cl.O>CO>[NH2:5][C:3]([NH:2][N:1]=[C:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:12][CH2:11][C:10]([NH:9][CH:7]([CH3:8])[CH3:6])=[O:21])=[S:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723789Thiosemicarbazide2×HCID 11009471HCID 11009471, compound

Product 1

HCID 53966896HCID 53966896, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide (2.08 g, 22.8 mmol) was added to a solution of N-(1-methylethyl)-4-oxo-4-phenyl-butyramide (5.0 g, 22.8 mmol), prepared in the previous step, in 80 ml of methanol plus 6.2 ml of 1 N HCl plus 6.2 ml of water and the reaction stirred at room temperature for 2 days. An additional 1.04 g (11.4 mmol) of thiosemicarbazide was added and the reaction stirred at room temperature for 24 hours. The reaction was cooled in an ice bath and a white solid precipitated. The solid was collected by filtration and dried. Recrystallization of the solid from isopropyl alcohol gave the title compound (4.73 g, 53%) as a white solid, mp 66-71° 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
  5. customRecrystallization of the solid from isopropyl alcohol

Sources & evidence

ORD record
ord-ea612a10696542f392c7bff1dad1dcbd
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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