N-Iodosuccinimide → 5-Amino-4-iodo-3-methyl-1-(2,4,6-trichlorophenyl)pyrazole

HRID 1421277

Reaktionsgleichung

Reaktionsgleichung von HRID 1421277
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([CH3:16])[CH:3]=1.[I:17]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([CH3:16])[C:3]=1[I:17]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 20600323-Methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazol-5-amine

Produkt 1

HCID 187807205-Amino-4-iodo-3-methyl-1-(2,4,6-trichlorophenyl)pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred solution of 5-amino-3-methyl-1-(2,4,6-trichlorophenyl)pyrazole (WO-A-94/13643; 35 g) and N-iodosuccinimide (29 g) in acetonitrile (450 ml) was heated under reflux for 1.5 hours, then the reaction mixture allowed to cool and evaporated under reduced pressure. The residue was dissolved in dichloromethane and the solution washed successively with aqueous sodium thiosulphate solution, water and brine, then dried (Na2SO4) and evaporated under reduced pressure. The resulting dark coloured solid was triturated with hexane to yield the title compound as a pale orange solid, m.p. 135-137° C. δ(CDCl3): 2.25 (s,3H), 3.67 (br.s,2H), 7.49 (s,2H). MS (thermospray): M/Z [M+H] 401.4; C10H7Cl3 lN3 +H requires 401.88.

Aufarbeitung

  1. temperatureunder reflux for 1.5 hours
  2. temperatureto cool
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washthe solution washed successively with aqueous sodium thiosulphate solution, water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customwas triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-d239e1a860f941579e3fa5b60df0d72e
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06075043

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