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

HRID 613683

Reaction equation

HRID 613683 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.[C:13]1([NH:19][C:20](=[S:23])[NH:21][NH2:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][C:5](=[N:22][NH:21][C:20](=[S:23])[NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 2535334-ChlorobutyrophenoneHCID 730679Hydrazinecarbothioamide, N-phenyl-

Product 1

HCID 537472602-(4-Chloro-1-phenyl-butylidene)-N-phenyl-hydrazinecarbothioamideYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chlorobutyrophenone (6.7 mL, 42 mmol) and 4-phenyl-3-thiosemicarbazide (7.0 g, 42 mmol) in 500 mL of ethanol was warmed under a nitrogen atmosphere to dissolve all the solids and then the reaction stirred at room temperature for four days. The solid formed was collected by filtration and dried under reduced pressure to give 8.73 g of a white solid. Recrystallization of the solid from ethanol gave 7.99 g (57%) of the title compound as a white solid, mp 107-109° C.

Workup

  1. temperaturewas warmed under a nitrogen atmosphere
  2. dissolutionto dissolve all the solids
  3. customThe solid formed
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a4ace6d1b5ed443c8dd624f2fd2543b9
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Linked notes

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