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

HRID 68702Notes

Reaction equation

HRID 68702 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[C:4]([F:11])[CH:3]=1.[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:19]\[NH:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH3:9])=[C:4]([F:11])[CH:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:19]/[NH:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH3:9])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 219385811-(4-Bromo-2-fluorophenyl)ethan-1-one

Product 2

HCID 86658771(Z)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazineHCID 86658772(E)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 500-mL round-bottom flask, was placed a solution of 1-(4-bromo-2-fluorophenyl)ethanone (17 g, 78.34 mmol, 1.00 equiv) in ethanol (200 mL), 1-phenylhydrazine (8.5 g, 78.70 mmol, 1.00 equiv), TSA-H2O (740 mg, 3.89 mmol, 0.05 equiv). The resulting solution was heated to reflux for 2 h in an oil bath, then concentrated under vacuum to yield (Z)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazine and (E)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazine as a yellow solid. MS (m/z): 307 [M+H]+

Workup

  1. customInto a 500-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 2 h in an oil bath
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c29c149380ad4496a1af2a5a7e4c27bf
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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