Methylhydrazine → 1-[1-(4-Fluorophenyl)-2-methylsulfonylethylidene]-2-methylhydrazine

HRID 335436Notes

Reaction equation

HRID 335436 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:4][CH:3]=1.[CH3:15][NH:16][NH2:17]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:17][NH:16][CH3:15])[CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 14882461-(4-Fluorophenyl)-2-(methylsulfonyl)-1-ethanone

Product 1

HCID 866893531-[1-(4-Fluorophenyl)-2-methylsulfonylethylidene]-2-methylhydrazineYield 31.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 50 ml volume three-necked flask, 1-(4-fluorophenyl)-2-methylsulfonylethan-1-one (7-2-3) (5.0 g), methylhydrazine (14-a) (1.2 g), and ethanol (17.1 ml) were added under a nitrogen atmosphere, and heated to reflux for 4 hours. After the mixture was cooled, the precipitated solid was removed by filtration. The filtrate was concentrated under reduced pressure. To the residue was added hot hexane to be dissolved. The mixture was left to cool. Then, the precipitated crystals were collected by filtration, washed, and dried under reduced pressure. The crystal was purified by recrystallization (methanol) to give 1.8 g of 1-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-2-methylhydrazine (5-2-4).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter the mixture was cooled
  4. customthe precipitated solid was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added hot hexane
  7. dissolutionto be dissolved
  8. waitThe mixture was left
  9. temperatureto cool
  10. filtrationThen, the precipitated crystals were collected by filtration
  11. washwashed
  12. customdried under reduced pressure
  13. customThe crystal was purified by recrystallization (methanol)

Sources & evidence

ORD record
ord-d148d772ec7a4c2a9691472ccb15f1a3
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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