Ethyl orthoformate → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneamino-4-trifluoromethylthiopyrazole

HRID 1078431

Reaktionsgleichung

Reaktionsgleichung von HRID 1078431
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21][C:22]([F:25])([F:24])[F:23].[CH:26](OCC)(OCC)[O:27][CH2:28][CH3:29]>CC1C=CC=CC=1>[C:19]([C:4]1[C:3]([S:21][C:22]([F:25])([F:24])[F:23])=[C:2]([N:1]=[CH:26][O:27][CH2:28][CH3:29])[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=1)#[N:20]

Komponenten

4

Edukt 2

HCID 31214Ethyl orthoformateHCID 9953940Fipronil sulfide

Produkt 1

HCID 540930933-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneamino-4-trifluoromethylthiopyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole (4.0 g) was added to triethyl orthoformate (19.0 ml) and p-toluene/-sulphonic acid (0.019 g) added. The mixture was heated under reflux for 21 hours, cooled, and the triethyl orthoformate evaporated in vacuo to give a brown oil as residue. This was purified by chromatography eluting with a mixture of dichloromethane and hexane (1:1). Evaporation of the eluates in vacuo gave 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneamino-4-trifluoromethylthiopyrazole as a colourless solid, m.p. 70°-71.5° C.

Aufarbeitung

  1. additionadded
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 21 hours
  4. temperaturecooled
  5. customthe triethyl orthoformate evaporated in vacuo
  6. customto give a brown oil as residue
  7. customThis was purified by chromatography
  8. washeluting with a mixture of dichloromethane and hexane (1:1)
  9. customEvaporation of the eluates in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e33311c729414d4989c4ed3b87a8673e
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05547974

Verknüpfte Notizen

Wird geladen…