Water → 1-(2-Fluoro-5-methoxybenzylidene)-2-(4-fluorophenyl)hydrazine

HRID 13187

Reaction equation

HRID 13187 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:12]=1[CH:13]=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:10][C:11]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:12]=1[CH:13]=[N:9][NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 69982(4-Fluorophenyl)hydrazineHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 668125981-(2-Fluoro-5-methoxybenzylidene)-2-(4-fluorophenyl)hydrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-fluorophenyl)hydrazine (6.5 g, 40 mmol), 2-fluoro-5-methoxybenzaldehyde (6.2 g, 40 mmol) and cesium carbonate (13 g, 40 mmol) were stirred in DMF (40 mL) at r.t. under argon atmosphere for 1.5 h and was then poured with stirring into water and extracted with ethyl acetate. The organic phase was washed trice with water, then brine and evaporated. The residue crystallized slowly to afford the subtitle compound as a beige-light brown crystal mass (10.21 g).

Workup

  1. additionwas then poured
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed trice with water
  4. custombrine and evaporated
  5. customThe residue crystallized slowly

Sources & evidence

ORD record
ord-5de05775b2444b41b706539db408683e
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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