[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine → [5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methylsulfanyl-1H-pyrazol-4-yl]-(2,5-dimethylphenyl)methanone

HRID 1279275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1279275
CS[C:3]([S:17][CH3:18])=[C:4]([C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[CH3:15])[C:5]#[N:6].[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([Cl:30])[C:21]=1[NH:31][NH2:32]>C(O)C>[NH2:6][C:5]1[N:31]([C:21]2[C:22]([Cl:30])=[CH:23][C:24]([C:26]([F:27])([F:28])[F:29])=[CH:25][C:20]=2[Cl:19])[N:32]=[C:3]([S:17][CH3:18])[C:4]=1[C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[CH3:15]

Komponenten

4

Edukt 2

HCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 158952653,3-Bis-methylthio-2-(2,5-dimethylbenzoyl)-acrylonitrile

Produkt 1

HCID 10183914[5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methylsulfanyl-1H-pyrazol-4-yl]-(2,5-dimethylphenyl)methanoneAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 7.94 g (28.6 mmol) of the product of step C and 7.01 g (28.6 mmol) of 2,6-dichloro-4-trifluoromethylphenylhydrazine in 100 mL of ethanol was heated at reflux for 2 hours, solution occurring as the reaction mixture was warmed. Then the ethanol was mostly removed on the rotary evaporator and the residues were partitioned between dilute aqueous hydrogen chloride solution and ethyl acetate. The organic phase was washed once with water and with brine, then dried with magnesium sulfate and treated with decolorizing carbon. The filtered solution was evaporated and the residues crystallized from 10:1 hexane/ethyl acetate to give 12.00 g (88%) of the title product in two crops, m.p. 130-132° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperaturewas warmed
  4. customThen the ethanol was mostly removed on the rotary evaporator
  5. customthe residues were partitioned between dilute aqueous hydrogen chloride solution and ethyl acetate
  6. washThe organic phase was washed once with water and with brine
  7. dry with materialdried with magnesium sulfate
  8. additiontreated with decolorizing carbon
  9. customThe filtered solution was evaporated
  10. customthe residues crystallized from 10:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b25dd54c231b4bb39d22bcb5ab2ff3e0
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448265B1

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