1,2-Dichlorobenzene → 5-[3-chloro-4-(5-trifluoromethylpyridine-2-yloxy)phenyl]-3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazole

HRID 1940735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940735
[CH3:1][N:2](S(C1C=CC=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[F:12].[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][N:34]=1)[C:27]#[N:28].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]([C:27]2[N:2]([CH3:1])[N:3]=[C:4]([C:5]3[C:6]([F:12])=[CH:7][CH:8]=[CH:9][C:10]=3[F:11])[N:28]=2)[CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:40])([F:41])[F:42])=[CH:35][N:34]=1

Komponenten

6

Edukt 3

HCID 72391,2-DichlorobenzeneHCID 214636733-Chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrileHCID 53707170N-methyl-N-(benzenesulfonyl)-2,6-difluorobenzohydrazonoyl chloride

Produkt 1

HCID 214636745-[3-chloro-4-(5-trifluoromethylpyridine-2-yloxy)phenyl]-3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazoleAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24380Iron chloride (FeCl3)KatalysatorHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of N-methyl-N-(benzenesulfonyl)-2,6-difluorobenzohydrazonoyl chloride (1.72 g), 3-chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrile (1.50 g), anhydrous iron (III) chloride (0.85 g) and o-dichlorobenzene (10 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, it is dissolved in chloroform (200 ml) and washed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline. Then, it is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography using mixed solvent of hexane-ethyl acetate as eluent and washed with hexane to give 1.25 g of desired compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline
  3. dry with materialThen, it is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate is purified by silica gel column chromatography
  6. additionusing mixed solvent of hexane-ethyl acetate as eluent
  7. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-1c73248cc80940cbb7b9acdb85c3f144
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700824

Notizen zur Reaktion

Wird geladen…