Reaktion #1511419

Reaktionsgleichung

benzyl bromide

DMSO

4-tert-butyl-2-nitrophenylamine

potassium hydroxide

→

title compound

Ausbeute 63.9%

Benzyl-(4-tert-butyl-2-nitrophenyl)amine

Ausbeute 63.9%

Lösungsmittel

Toluene

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for another twenty minutes
2. 2
   TemperaturAfter cooling to 10° C.
3. 3
   workup.STIRRINGthe reaction mixture was stirred for 4 hours
4. 4
   workup.STIRRINGthe mixture stirred for 30 minutes
5. 5
   ExtraktionThe aqueous layer was extracted with toluene (2×10 L)
6. 6
   Einengenthe combined organic extracts concentrated under vacuum at <50° C
7. 7
   workup.ADDITIONIsopropanol (4 L) was added
8. 8
   Temperaturthe mixture cooled to −5° C
9. 9
   workup.STIRRINGThe slurry was stirred for 1 hour
10. 10
    Sonstigebefore collecting the solids
11. 11
    Filtrationby filtration
12. 12
    Waschenwashing with isopropanol (2×1.5 L)
13. 13
    Sonstigedrying at 55-60° C.

Vorschrift

A reactor was charged with DMSO (6 L), followed by 4-tert-butyl-2-nitrophenylamine (Preparation 108, 3.0 kg, 15.4 mol) and potassium hydroxide (1.32 kg, 23.5 mol). The mixture was stirred at room temperature for twenty minutes. Toluene (12 L) was added and the mixture stirred for another twenty minutes. After cooling to 10° C., benzyl bromide (3.16 kg, 18.5 mol) was added slowly and the reaction mixture was stirred for 4 hours. Water (30 L) was added, the mixture stirred for 30 minutes and the layers allowed to settle. The aqueous layer was extracted with toluene (2×10 L), followed by ethyl acetate (10 L), and the combined organic extracts concentrated under vacuum at <50° C. Isopropanol (4 L) was added and the mixture cooled to −5° C. The slurry was stirred for 1 hour before collecting the solids by filtration, washing with isopropanol (2×1.5 L) and drying at 55-60° C. to provide 2.8 kg of the title compound.

Quelle