反応 #1511419

反応方程式

benzyl bromide

DMSO

4-tert-butyl-2-nitrophenylamine

potassium hydroxide

→

title compound

収率 63.9%

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

収率 63.9%

溶媒

Toluene

Water

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred for another twenty minutes
2. 2
   温度After 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
   抽出The aqueous layer was extracted with toluene (2×10 L)
6. 6
   濃縮the combined organic extracts concentrated under vacuum at <50° C
7. 7
   workup.ADDITIONIsopropanol (4 L) was added
8. 8
   温度the mixture cooled to −5° C
9. 9
   workup.STIRRINGThe slurry was stirred for 1 hour
10. 10
    その他before collecting the solids
11. 11
    ろ過by filtration
12. 12
    洗浄washing with isopropanol (2×1.5 L)
13. 13
    その他drying at 55-60° C.

実験手順

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.

出典