4-Chlorobutyrophenone → 2-(4-Chloro-1-phenyl-butylidene)-hydrazinecarbothioamide

HRID 613684Notes

Reaction equation

HRID 613684 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][CH:15]=[CH:14][CH:13]=1)=O>CO.Cl.O>[Cl:6][CH2:7][CH2:8][CH2:9][C:10](=[N:1][NH:2][C:3](=[S:4])[NH2:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 2535334-ChlorobutyrophenoneHCID 2723789Thiosemicarbazide

Product 1

HCID 544845622-(4-Chloro-1-phenyl-butylidene)-hydrazinecarbothioamideYield 68.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Thiosemicarbazide (9.11 g, 0.1 mol) was added under nitrogen to a solution of 4-chlorobutyrophenone (16 mL, 0.1 mol) in 350 mL of methanol plus 27 mL of 1 N HCl plus 25 mL of water. After approximately 30 minutes of stirring at room temperature, all of the solid had dissolved. The reaction was then stirred at room temperature for 24 hours (overnight). The solid that had formed was collected by filtration and dried under high vacuum to give 17.41 g (68%) of the title compound as a white solid, mp 128-130° C.

Workup

  1. dissolutionall of the solid had dissolved
  2. stirringThe reaction was then stirred at room temperature for 24 hours (overnight)
  3. customThe solid that had formed
  4. filtrationwas collected by filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-8c30833b289d4bc48a4990f341d6cbe5
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Reaction notes

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