Water → 4-(1-Pyrazolyl)benzonitrile

4-Fluorobenzonitrile (204.2 g), pyrazole (138.6 g, 1.22 eq) and potassium carbonate (281.5 g, 1.22 eq) in DMF (1110 ml) were heated at 120° C. for 7 hours. The suspension was cooled to 25° C. and water (2920 ml) added. The reaction was extracted with MTBE (3×1460 ml) and the combined extracts were washed with water (3×1460 ml) and saturated aqueous sodium chloride (1460 ml). The organic phase was concentrated at atmospheric pressure until the pot temperature rose to 65° C. Heptane (1700 ml) was added over 30 minutes at 60-65° C., and then a further 300 ml of distillate was collected. The solution was stirred at 60-65° C. for 15 minutes and then cooled to <5° C. The slurry was filtered and washed with heptane (2×200 ml), and dried under vacuum to constant weight to give the title compound as a solid (245.3 g, 87%).

1. extractionThe reaction was extracted with MTBE (3×1460 ml)
2. washthe combined extracts were washed with water (3×1460 ml) and saturated aqueous sodium chloride (1460 ml)
3. concentrationThe organic phase was concentrated at atmospheric pressure until the pot temperature
4. customrose to 65° C
5. additionHeptane (1700 ml) was added over 30 minutes at 60-65° C.
6. distillationa further 300 ml of distillate was collected
7. temperaturecooled to <5° C
8. filtrationThe slurry was filtered
9. washwashed with heptane (2×200 ml)
10. customdried under vacuum to constant weight

ORD 기록

ord-f3646d6af89c48f69ce8da0f827321e2

출처 데이터셋

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08466284B2