Hydrochloric Acid → HCID 54330722, compound

HRID 1636635Notes

Reaction equation

HRID 1636635 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].O=[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13].Cl.O>CO>[NH2:5][C:3]([NH:2][N:1]=[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[S:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723789ThiosemicarbazideHCID 10488465HCID 10488465, compound

Product 1

HCID 54330722HCID 54330722, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiosemicarbazide (2.85 g, 31.3 mmol) was added to a solution of N-(4-oxo-4-phenyl-butyl)-acetamide (4.28 g, 20.9 mmol), prepared in the previous step, in 75 ml of methanol plus 5.6 ml of 1 N HCl, plus 5.6 ml of water and the reaction stirred at room temperature for 42 hours. 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 4.77 g of a yellow solid Recrystallization of this solid from ethyl acetate gave the title compound (3.53 g, 61%) as an off-white solid, mp 74-83° 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
  8. customto give
  9. custom4.77 g of a yellow solid Recrystallization of this solid from ethyl acetate

Sources & evidence

ORD record
ord-9aad17d3adce406cb6e420535c8f59ba
Source dataset
uspto-grants-2000_03
Patent number
US06034272

Reaction notes

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