Hydrazine → HCID 178509108, 화합물

HRID 1060961노트

반응식

HRID 1060961 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:10]#[N:11])=[CH:4][CH:3]=1.P(Cl)(Cl)Cl.[NH2:23][NH2:24]>C(#N)C>[NH2:11][C:10]1[NH:24][N:23]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 9321HydrazineHCID 24387Phosphorus trichlorideHCID 220374773-(4-Chlorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile

생성물 1

HCID 178509108HCID 178509108, 화합물수율 54.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 3-(4-chlorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile (3.50 g, 13.6 mmol) in 40 mL acetonitrile and phosphorous trichloride (14.2 ml, 163 mmol) was stirred at 100° C. for 5 hours. The reaction mixture was concentrated in vacuo, and the residue taken up in toluene and concentrated again. The residue was then taken up in ethanol (150 mL) and treated with anhydrous hydrazine (1.71 mL, 54.4 mmol). The reaction mixture was heated to reflux for 3 hours, cooled, and concentrated in vacuo. The residue was triturated with a mixture of ethanol and dichloromethane (1:4), and filtered. The solid was washed with the ethanol/dichloromethane mixture, and dried to give 5-amino-3-(4-chlorophenyl)-4-(pyridin-4-yl)-pyrazole (2.0 g, 54%): m.p.>300° C. 1H NMR (DMSO/300 MHz) δ8.40 (d, 2H), 7.40 (d, 2H), 7.29 (d, 2H), 7.11 (d, 2H), 5.05 (s, 2H). ESLRMS m/z 271 (M+H). ESHRMS m/z 271.0752 (M+H, C14H11N4Cl requires 271.0750).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. concentrationconcentrated again
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 3 hours
  5. temperaturecooled
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with a mixture of ethanol and dichloromethane (1:4)
  8. filtrationfiltered
  9. washThe solid was washed with the ethanol/dichloromethane mixture
  10. customdried

출처 및 근거

ORD 기록
ord-f15da0f6726b4ad286a3c960d1f8485c
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525059B1

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