4-Chloro-4'-methoxybutyrophenone → HCID 54139554, compound

HRID 613688Notes

Reaction equation

HRID 613688 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[Cl:6][CH2:7][CH2:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=O>CO.Cl.O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10](=[N:1][NH:2][C:3](=[S:4])[NH2:5])[CH2:9][CH2:8][CH2:7][Cl:6])=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 964144-Chloro-4'-methoxybutyrophenoneHCID 2723789Thiosemicarbazide

Product 1

HCID 54139554HCID 54139554, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Thiosemicarbazide (6.4 g, 70 mmol) was added under nitrogen to a solution of 4-chloro-4'-methoxybutyrophenone (10.0 g, 47 mmol) in 150 mL of methanol plus 12.7 mL of 1 N HCl plus 11.8 mL of water and the reaction stirred for approximately three days (over the weekend). The solid formed was collected by filtration and dissolved in methylene chloride. The organic solution was washed multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give a white solid. Recrystallization of the solid from isopropyl alcohol gave 8.46 g (63%) of the title compound as a light yellow solid, mp 137-140° C.

Workup

  1. customThe solid formed
  2. filtrationwas collected by filtration
  3. dissolutiondissolved in methylene chloride
  4. washThe organic solution was washed multiple times with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customto give a white solid
  8. customRecrystallization of the solid from isopropyl alcohol

Sources & evidence

ORD record
ord-473cda8ab1774408aa851f7ddb04809a
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Reaction notes

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