4-Chloro-4'-methylbutyrophenone → 2-[1-(4-Methyl-phenyl)-4-chloro-butylidene]-hydrazinecarbothioamide

HRID 613687Notes

Reaction equation

HRID 613687 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]([CH3:18])=[CH:14][CH:13]=1)=O>CO.Cl.O>[CH3:18][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 987454-Chloro-4'-methylbutyrophenoneHCID 2723789Thiosemicarbazide

Product 1

HCID 541274022-[1-(4-Methyl-phenyl)-4-chloro-butylidene]-hydrazinecarbothioamideYield 75.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Thiosemicarbazide (6.84 g, 75 mmol) was added under nitrogen to a solution of 4-chloro-4'-methylbutyrophenone (10.0 g, 50 mmol) in 175 mL of methanol plus 13.5 mL of 1 N HCl plus 12.5 mL of water and the reaction stirred at room temperature overnight. 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 10.15 g of an off-white solid. Recrystallization of the solid from isopropyl alcohol gave 8.65 g (64%) of the tide compound as an off-white solid, mp133-135° 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

Sources & evidence

ORD record
ord-5f1abbbe2bbd47828c907cf2310e5e60
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Reaction notes

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