Fenbuconazole → 4-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]-1-butylamine

HRID 2211091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2211091
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](C2C=CC=CC=2)([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[C:17]#[N:18])=[CH:10][CH:9]=1>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH:16]([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:17][NH2:18])=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 86138FenbuconazoleHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 199569544-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]-1-butylamineAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a 5 liter flask stirring under nitrogen, fitted with a mechanical stirrer, was charged 18 g (0.45 mole) of lithium aluminum hydride in 1000 mL of dry tetrahydrofuran which was then cooled to 5° C. To the slurry was added 152 g (0.45 mole) of alpha-(2-(4-chlorophenyl)ethyl)-alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile in 2000 mL of dry tetrahydrofuran over 3 hours. The reaction was kept at 5°-10° C. during the addition then allowed to warm to room temperature and stirred overnight. The reaction was cooled in an ice bath and quenched with the slow addition of sodium sulfate. The solvent was removed and the residue was extracted with ethyl acetate and washed with 1000 mL water and 1000 mL brine. After drying, and removal of the solvent, 137 g (89.5% yield) of a very viscous oil resulted.

Aufarbeitung

  1. customfitted with a mechanical stirrer
  2. additionThe reaction was kept at 5°-10° C. during the addition
  3. temperatureto warm to room temperature
  4. stirringstirred overnight
  5. temperatureThe reaction was cooled in an ice bath
  6. customquenched with the slow addition of sodium sulfate
  7. customThe solvent was removed
  8. extractionthe residue was extracted with ethyl acetate
  9. washwashed with 1000 mL water and 1000 mL brine
  10. customAfter drying
  11. customremoval of the solvent, 137 g (89.5% yield) of a very viscous oil
  12. customresulted

Quellen und Nachweise

ORD-Eintrag
ord-fac1dc8f00a84ea69532b820c2c8f221
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05462931

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