2,2,2-Trifluoroethylhydrazine → 4,5-Dichloro-2-(2,2,2-trifluoroethyl)-3(2H)-pyridazinone

HRID 381899

Reaction equation

HRID 381899 reaction equation
[F:1][C:2]([F:7])([F:6])[CH2:3][NH:4][NH2:5].[C:8](O)(=[O:15])/[C:9](=[C:11](\[CH:13]=O)/[Cl:12])/[Cl:10]>C(O)C>[F:1][C:2]([F:7])([F:6])[CH2:3][N:4]1[C:8](=[O:15])[C:9]([Cl:10])=[C:11]([Cl:12])[CH:13]=[N:5]1

Participants

4

Reactant 2

HCID 787402,2,2-TrifluoroethylhydrazineHCID 2771871Mucochloric Acid

Product 1

HCID 138815564,5-Dichloro-2-(2,2,2-trifluoroethyl)-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,2,2-Trifluoroethylhydrazine (70% solution in water, 35.0 g, 0.307 mol) was treated with mucochloric acid (51.88 g, 0.307 mol) in ethanol (300 mL) and refluxed for 5 hours. The solvent was concentrated in vacuo. The crystals obtained were washed with water and air dried (yield: 50 g; 67.5%). 1H NMR (300 MHz, CDCl3) δ 4.8 (q, J=9 Hz, 2H), 7.85 (s, 1H). MS (DCl-NH3) m/z 264 (M+NH4)+.

Workup

  1. temperaturerefluxed for 5 hours
  2. concentrationThe solvent was concentrated in vacuo
  3. customThe crystals obtained
  4. washwere washed with water and air
  5. customdried (yield: 50 g; 67.5%)

Sources & evidence

ORD record
ord-b275da0cabc342c7b5e85ec7bdd06e4d
Source dataset
uspto-grants-2001_10
Patent number
US06307047B1

Linked notes

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