Hydrochloric Acid → HCID 54230298, compound

HRID 1636632Notes

Reaction equation

HRID 1636632 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH:6]([N:9]([CH2:13][CH2:14][CH2:15][C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:10](=[O:12])[CH3:11])([CH3:8])[CH3:7].Cl.O>CO>[NH2:5][C:3]([NH:2][N:1]=[C:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:15][CH2:14][CH2:13][N:9]([CH:6]([CH3:8])[CH3:7])[C:10](=[O:12])[CH3:11])=[S:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723789ThiosemicarbazideHCID 19352253HCID 19352253, compound

Product 1

HCID 54230298HCID 54230298, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide (6.1901 g, 67.9 mmol) was added to a solution of N-isopropyl-N-(4-oxo-4-phenyl-butyl)-acetamide (11.20 g, 45.3 mmol), prepared in the previous step, in 160 ml of methanol plus 12.2 ml of 1 N HCl, plus 12.2 ml of water and the reaction stirred at room temperature for 22 hours (overnight). The reaction was concentrated under reduced pressure to remove the methanol. The residue was partitioned between methylene chloride and water. The organic layer was separated, washed five times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 14.54 g of a yellow foam. The foam was crystallized from ethyl acetate to give 10.28 g (71%) of the title compound as a white solid, mp 141-147° C.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove the methanol
  3. customThe residue was partitioned between methylene chloride and water
  4. customThe organic layer was separated
  5. washwashed five times with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-fc0ad5ca248f4ef3868706dfdd397aa1
Source dataset
uspto-grants-2000_03
Patent number
US06034272

Reaction notes

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