Dichloromethane → 1-(2-Chlorophenyl)-5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazole

温度

60 °C

To a solution of 1-(2-furyl)-4,4,4-trifluorobutane-1,3-dione (105 g, 0.51 mole) in glacial acetic acid (220 mL) was added sodium acetate (42 g 0.51 mole). The temperature rose to about 34° C. 2-Chlorophenylhydrazine hydrochloride (90 g, 0.5 mole) was added portionwise over a period of 10 minutes to give a creamy suspension. The mixture was warmed to about 60° C. for about 45 minutes. The bulk of the acetic acid was removed by stripping on a rotary evaporator at a bath temperature of 65° C. The remaining oily residue was added to about 800 ml of water with vigorous stirring and a heterogeneous mixture resulted. After about 15 minutes, dichloromethane (500 mL) was added and the mixture was partitioned. The aqueous phase was extracted with 300 ml of dichloromethane. The combined organic phases were washed with water and saturated sodium bicarbonate solution and then dried with MgSO4 and filtered. Volatiles were removed on a rotary evaporator. The crude product consisted of 151 g of a dark red oil, which contained approximately 89% of the desired product and 11% of the regioisomeric pyrazole (determined by NMR analysis).

1. customrose to about 34° C
2. customto give a creamy suspension
3. customThe bulk of the acetic acid was removed
4. customby stripping on a rotary evaporator at a bath temperature of 65° C
5. additionThe remaining oily residue was added to about 800 ml of water
6. customa heterogeneous mixture resulted
7. customthe mixture was partitioned
8. extractionThe aqueous phase was extracted with 300 ml of dichloromethane
9. washThe combined organic phases were washed with water and saturated sodium bicarbonate solution
10. dry with materialdried with MgSO4
11. filtrationfiltered
12. customVolatiles were removed on a rotary evaporator

ORDレコード

ord-a62594dca20f4e3bb2f3c4e18e2143ed

出典データセット

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07326704B2