Methylhydrazine → 1-(2,4-Dibromo-5-(2-fluoro-4-nitrophenoxy)benzylidene)-2-methylhydrazine

HRID 2195490Notes

Reaction equation

HRID 2195490 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Br:10])[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])=[CH:6][C:3]=1[CH:4]=O.[CH3:22][NH:23][NH2:24]>C1COCC1>[Br:1][C:2]1[CH:9]=[C:8]([Br:10])[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])=[CH:6][C:3]=1[CH:4]=[N:24][NH:23][CH3:22]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 866384722,4-Dibromo-5-(2-fluoro-4-nitrophenoxy)benzaldehyde

Product 1

HCID 667671401-(2,4-Dibromo-5-(2-fluoro-4-nitrophenoxy)benzylidene)-2-methylhydrazineYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dibromo-5-(2-fluoro-4-nitrophenoxy)benzaldehyde (13.0 g, 31.0 mmol) is refluxed with methylhydrazine (4.3 g, 93 mmol) in THF (130 mL) for 2 hours. The reaction is quenched with water (150 mL) and extracted with MTBE (2×150 mL). The organic layer is washed with saturated sodium chloride aqueous solution (2×150 mL), dried with anhydrous sodium sulfate, and concentrated to obtain a solid. The crude solid is recrystallized in EtOAc/hexane to obtain 1-(2,4-dibromo-5-(2-fluoro-4-nitrophenoxy)benzylidene)-2-methylhydrazine as a yellow solid (10.6 g, 76.7% yield). MS (m/z): 447.9 (M+H).

Workup

  1. customThe reaction is quenched with water (150 mL)
  2. extractionextracted with MTBE (2×150 mL)
  3. washThe organic layer is washed with saturated sodium chloride aqueous solution (2×150 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain a solid
  7. customThe crude solid is recrystallized in EtOAc/hexane

Sources & evidence

ORD record
ord-08f36f1c98aa4dd29b4e989adf9c47eb
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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