Ethanol → 4-Chloro-4'-methylmercaptomethylbenzophenone hydrazone

HRID 1421539Notes

Reaction equation

HRID 1421539 reaction equation
C(O)C.[Cl:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][S:18][CH3:19])=[CH:13][CH:12]=2)=O)=[CH:7][CH:6]=1.O.[NH2:23][NH2:24]>C(O)(=O)C>[Cl:4][C:5]1[CH:21]=[CH:20][C:8]([C:9](=[N:23][NH2:24])[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][S:18][CH3:19])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 196893654-Chloro-4'-methylthiomethylbenzophenone

Product 1

HCID 857041584-Chloro-4'-methylmercaptomethylbenzophenone hydrazone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

An ethanol solution (50 ml) of 4-chloro-4'-methylmercaptomethylbenzophenone (9.3 g), hydrazine hydrate (6 ml) and acetic acid (3 ml) was heated for 20 hours with refluxing. The solvent was distilled off under reduced pressure, and then the obtained oily substance was diluted with dichloromethane and washed successively with an aqueous 5% sodium hydroxide solution, water and an aqueous saturated a sodium chloride solution, followed by drying over anhydrous magnesium sulfate. The solvent was then distilled off to obtain 4-chloro-4'-methylmercaptomethylbenzophenone hydrazone (7.1 g) as an isomer mixture (syn form/anti form=about 1:1).

Workup

  1. temperaturewith refluxing
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe obtained oily substance was diluted with dichloromethane
  4. washwashed successively with an aqueous 5% sodium hydroxide solution, water
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-b4880628523d40589c54c791d294a04f
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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