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

HRID 857853

반응식

HRID 857853 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][C:8](=O)[C:9]([F:12])([F:11])[F:10].C([O-])(=O)C.[Na+].Cl.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][NH2:29].ClCCl>C(O)(=O)C>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][C:8]([C:9]([F:12])([F:11])[F:10])=[N:29]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 517045Sodium Acetate

생성물 1

HCID 574582361-(2-Chlorophenyl)-5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazole

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4c0e29ade87c47c281c9615a1b72c9c9
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148217B2

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