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

HRID 1940730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940730
[CH3:1][N:2](S(C1C=CC=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[Cl:22][C:23]1[CH:30]=[C:29]([O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][N:33]=2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Cl:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]1[N:26]=[C:25]([C:24]2[CH:27]=[CH:28][C:29]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:34][N:33]=3)=[CH:30][C:23]=2[Cl:22])[N:2]([CH3:1])[N:3]=1

Komponenten

6

Edukt 3

HCID 72391,2-DichlorobenzeneHCID 214636072-Chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrileHCID 54508988N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride

Produkt 1

HCID 214636273-(2-chlorophenyl)-5-[2-chloro-4-(5-trifluoromethylpyridine-2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazoleAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24380Iron chloride (FeCl3)KatalysatorHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of N-methyl-N-(benzenesulfonyl)-2-chlorobenzohydrazonoyl chloride (2.05 g), 2-chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrile (1.88 g), anhydrous iron (III) chloride (1.07 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 (300 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 to give 1.87 g of desired compound (melting point: 104.0°-108.0° C.).

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

Quellen und Nachweise

ORD-Eintrag
ord-1154b77a029143369d78e2d011a31703
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700824

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