Ethanol → 3-tert-butyl-1-(3-phenoxyphenyl)-1H-pyrazol-5-amine

HRID 16997

반응식

HRID 16997 반응식
[O:1]([C:8]1[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:15]([O-])=O.[Na+].[CH3:19][C:20]([CH3:27])([CH3:26])[C:21](=O)[CH2:22][C:23]#[N:24].CCO>O.Cl>[C:20]([C:21]1[CH:22]=[C:23]([NH2:24])[N:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)[N:15]=1)([CH3:27])([CH3:26])[CH3:19]

참가 물질

7

반응물 4

HCID 702EthanolHCID 771353-PhenoxyanilineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 23668193Sodium Nitrite

생성물 1

HCID 184499043-tert-butyl-1-(3-phenoxyphenyl)-1H-pyrazol-5-amine수율 17.5%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

In a 250 mL Erlenmeyer flask with a magnetic stir bar, 3-phenoxyphenylamine (4.81 g, 0.026 mol) was added to 6 N HCl (40 mL) and cooled with an ice bath to 0° C. A solution of NaNO2 (2.11 g, 0.0306 mol, 1.18 eq.) in water (5 mL) was added drop wise. After 30 min, SnCl22H2O (52.0 g, 0.23 mol, 8.86 eq.) in 6 N HCl (100 mL) was added and the reaction mixture was allowed to stir for 3 h, and then subsequently transferred to a 500 mL round bottom flask. To this, 4,4-dimethyl-3-oxopentanenitrile (3.25 g, 0.026 mol) and EtOH (100 ml) were added and the mixture refluxed for 4 h, concentrated in vacuo and the residue extracted with EtOAc (2×100 mL) and purified by column chromatography using hexane/EtOAc/Et3N (8:2:0.2) to yield 3-tert-butyl-1-(3-phenoxyphenyl)-1H-pyrazol-5-amine (1.40 g, 17%). mp: 108-110° C.; 1H NMR (CDCl3): δ 7.3 (m, 10H), 5.7 (s, 1H), 4.9 (brs, 2H), 1.3 (s, 9H).

후처리

  1. customsubsequently transferred to a 500 mL round bottom flask
  2. temperaturethe mixture refluxed for 4 h
  3. concentrationconcentrated in vacuo
  4. extractionthe residue extracted with EtOAc (2×100 mL)
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-7e331da8788e46678e390a85581c3e47
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737283B2

연결된 노트

불러오는 중…