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

HRID 52238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52238
[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].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][N:35]=1.ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[F:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([F:12])[C:5]=1[C:4]1[N:30]=[C:29]([C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[C:26]([O:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:42])([F:43])[F:41])=[CH:36][N:35]=3)[CH:27]=2)[N:2]([CH3:1])[N:3]=1

Komponenten

6

Edukt 3

HCID 72391,2-DichlorobenzeneHCID 214636784-Methoxy-3-(5-trifluoromethylpyridine-2-yloxy)benzonitrileHCID 53707170N-methyl-N-(benzenesulfonyl)-2,6-difluorobenzohydrazonoyl chloride

Produkt 1

HCID 214636063-(2,6-difluorophenyl)-5-[4-methoxy-3-(5-trifluoromethylpyridine-2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazoleAusbeute 32 %

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 (0.70 g), 4-methoxy-3-(5-trifluoromethylpyridine-2-yloxy)benzonitrile (0.80 g), anhydrous iron (III) chloride (0.50 g) and o-dichlorobenzene (5 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, it is dissolved in chloroform (100 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 0.30 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

Quellen und Nachweise

ORD-Eintrag
ord-dba0fe32ae4f45adbc4469be2e4fac9f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616594

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