4-Chloro-4'-hydroxybutyrophenone → HCID 136171416, compound

HRID 613689Notes

Reaction equation

HRID 613689 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]([OH:18])=[CH:14][CH:13]=1)=O>CO.Cl.O>[OH: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 815784-Chloro-4'-hydroxybutyrophenoneHCID 2723789Thiosemicarbazide

Product 1

HCID 136171416HCID 136171416, compoundYield 61.3%

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'-hydroxybutyrophenone (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 room temperature for forty hours. The reaction was concentrated under reduced pressure to remove most of the methanol. The residue was partitioned between methylene chloride and water. The organic layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to give 8.33 g of a white solid. Recrystallization of the solid from isopropyl alcohol gave 3.19 g (21%) of the title compound as a light yellow solid, mp 126-129° C.

Workup

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

Sources & evidence

ORD record
ord-81fff50bba4948bd95e3c2bdd0358352
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Reaction notes

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