Phenylhydrazine → (Z)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine

HRID 68691Notes

Reaction equation

HRID 68691 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[C:4]([F:12])[CH:3]=1.[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:20]\[NH:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)/[CH2:9][CH3:10])=[C:4]([F:12])[CH:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:20]/[NH:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)/[CH2:9][CH3:10])=[C:4]([F:12])[CH:3]=1

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 185462181-(4-Bromo-2-fluorophenyl)propan-1-one

Product 2

HCID 86658768(Z)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazineHCID 86658769(E)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 1000-mL round-bottom flask, was placed a solution of 1-(4-bromo-2-fluorophenyl)propan-1-one (32 g, 138.53 mmol, 1.00 equiv) in ethanol (300 mL), 1-phenylhydrazine (15.0 g, 138.89 mmol, 1.00 equiv), TSA-H2O (1.32 g, 6.95 mmol, 0.05 equiv). The resulting solution was heated to reflux for 1 h in an oil bath. The resulting mixture was concentrated under vacuum to yield (Z)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine and (E)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine as a yellow solid. MS: 322 (MH+)

Workup

  1. customInto a 1000-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 1 h in an oil bath
  4. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-499c52bcb03e4853ae071418f2111c5c
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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