تفاعل #90324

معادلة التفاعل

[1,1′-biphenyl]-2-amine

oxalyl chloride

4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline

triethylamine

→

title compound

1-([1,1′-biphenyl]-2-yl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)urea

المذيبات

Tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىTo a three-necked round bottomed flask equipped with condenser and nitrogen inlet
2. 2
   workup.ADDITIONwas added to the reaction mixture
3. 3
   أخرىThe resulting reaction mixture
4. 4
   درجة الحرارةwas slowly warmed to room temperature
5. 5
   أخرىUpon completion, the reaction mixture was quenched with water (50 mL)
6. 6
   استخلاصextracted with ethyl acetate (150 mL×2)
7. 7
   غسيلThe organic phase was washed with brine (50 mL)
8. 8
   تجفيفThe combined organic layers were dried over sodium sulfate
9. 9
   تركيزwere then concentrated under reduced pressure
10. 10
    أخرىPurification by flash column chromatography

الإجراء التجريبي

To a three-necked round bottomed flask equipped with condenser and nitrogen inlet was charged with oxalyl chloride (0.378 g, 2.98 mmol). Tetrahydrofuran (25 mL) was added and the reaction was cooled to 0° C. 4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline (0.800 g, 2.50 mmol) and triethylamine (1.74 mL, 12.5 mmol) were added at 0° C. After 30 minutes, [1,1′-biphenyl]-2-amine (0.508 g, 3.00 mmol) dissolved in tetrahydrofuran (25 mL) was added to the reaction mixture. The resulting reaction mixture was slowly warmed to room temperature. Upon completion, the reaction mixture was quenched with water (50 mL) and extracted with ethyl acetate (150 mL×2). The organic phase was washed with brine (50 mL). The combined organic layers were dried over sodium sulfate and were then concentrated under reduced pressure. Purification by flash column chromatography using 0-30% ethyl acetate/hexanes provided the title compound as an off white solid (0.560 g, 87%).

المصدر