Ethanol → 4-Chloro-4'-methylsulfonylmethylbenzophenone-hydrazone

HRID 2093Notes

Reaction equation

HRID 2093 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.O.[NH2:22][NH2:23].C(O)C>C(O)(=O)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6](=[N:22][NH2:23])[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 187799134-Chloro-4'-methylsulfonylmethylbenzophenone

Product 1

HCID 867522794-Chloro-4'-methylsulfonylmethylbenzophenone-hydrazoneYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-chloro-4'-methylsulfonylmethylbenzophenone (10.0 g) and hydrazine monohydrate (4.9 g) were added to ethanol (200 ml) and acetic acid (10 ml), and the mixture was stirred for 6 hours under reflux. The reaction mixture was concentrated, and the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product (10.0 g, melting point: 52° to 54° C., yield: 97%)

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-4a998f07f4214c4e80efb60ca50f068e
Source dataset
uspto-grants-1998_03
Patent number
US05728699

Reaction notes

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