Phenylhydrazine → 1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-5-amine

HRID 1749137

반응식

HRID 1749137 반응식
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:10]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[CH2:11][C:12]#[N:13]>CO>[C:1]1([N:7]2[C:12]([NH2:13])=[CH:11][C:10]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 7516PhenylhydrazineHCID 1418532-Thenoylacetonitrile

생성물 1

HCID 162286411-phenyl-3-(thiophen-2-yl)-1H-pyrazol-5-amine수율 98.9%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
120 °C

실험 절차

Phenyl hydrazine (143 mg, 1.32 mmol) and 3-oxo-3-(2-thienyl)propionitrile (200 mg, 1.32 mmol) were placed in a microwave vial and dissolved in methanol (660 μL). The vial was sealed, placed in a microwave oven and heated at 120° C. for 40 minutes. After this period, the reaction mixture was concentrated to dryness in vacuo. The residue was redissolved in ethyl acetate and the organic solution washed with water, saturated aqueous NaHCO3 and brine, respectively. The organic layer was dried over anhydrous Na2SO4 and concentrated. The crude material was purified by flash chromatography (20-50% ethyl acetate/hexanes gradient) to afford the desired intermediate, 2-phenyl-5-thiophen-2-yl-2H-pyrazol-3-ylamine (315 mg).

후처리

  1. customThe vial was sealed
  2. customplaced in a microwave oven
  3. waitAfter this period
  4. concentrationthe reaction mixture was concentrated to dryness in vacuo
  5. dissolutionThe residue was redissolved in ethyl acetate
  6. washthe organic solution washed with water, saturated aqueous NaHCO3 and brine
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe crude material was purified by flash chromatography (20-50% ethyl acetate/hexanes gradient)

출처 및 근거

ORD 기록
ord-d42607bb229840899c6c74fe0c2abb04
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156775B2

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