4,4'-Dichlorobutyrophenone → 2-[1-(4-Chloro-phenyl)-4-chloro-butylidene]-hydrazinecarbothioamide

HRID 613686Notes

Reaction equation

HRID 613686 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]([Cl:18])=[CH:14][CH:13]=1)=O>CO.Cl.O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[N:1][NH:2][C:3](=[S:4])[NH2:5])[CH2:9][CH2:8][CH2:7][Cl:6])=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 27237814,4'-DichlorobutyrophenoneHCID 2723789Thiosemicarbazide

Product 1

HCID 537421812-[1-(4-Chloro-phenyl)-4-chloro-butylidene]-hydrazinecarbothioamideYield 69.7%

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 4,4'-dichlorobutyrophenone (21.7 g, 0.1 mol) in 350 mL of methanol plus 27 mL of 1N HCl plus 25 mL of water and the reaction stirred at room temperature for 21 hours (overnight). The solid was collected by filtration and dried to give 20.23 g of a white solid. Recrystallization of the solid from isopropyl alcohol gave 8.37 g (29%) of the title compound as a light yellow solid, mp 125-126° C.

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-bfe688eb48d145caa5f48d7023f608de
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Reaction notes

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