Sulfuric Acid → 2-(2-Ethyl-phenyl)-2H-pyrazol-3-ylamine

HRID 1526480

반응식

HRID 1526480 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10])[CH3:2].[CH2:11]([NH2:14])[CH:12]=[CH2:13].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>CO.C(N(CC(O)=O)CC(O)=O)CN(CC([O-])=O)CC([O-])=O.[Na+].[Na+]>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:11]([NH2:14])=[CH:12][CH:13]=[N:10]1)[CH3:2]

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 7853AllylamineHCID 10340Sodium CarbonateHCID 2733210(2-Ethylphenyl)hydrazine

생성물 1

HCID 675133942-(2-Ethyl-phenyl)-2H-pyrazol-3-ylamine수율 80%

시약·촉매·용매 2

HCID 13020083Ethylenediaminetetraacetic acid disodium salt촉매HCID 887Methanol용매

실험 절차

To a solution (2-Ethyl-phenyl)-hydrazine 1 (35 mmol) and disodium ethylenediaminetetraacetate (20 mg) in methanol (60 ml), 2-chloroacrylonitrile 2 (105 mmol) was added dropwise at 60° C., and the mixture was stirred under reflux for 8 hours. Then concentrated sulfuric acid (94 mmol) was added and the mixture was further heated for 6 hours. After cooling to room temperature the mixture was quenched with anhydrous sodium carbonate (105 mmol) and the solvent was removed under reduced pressure. The residue was treated with water (100 mL) and the product extracted with ethyl acetate (3*100 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography to give (28 mmol) of 2-(2-Ethyl-phenyl)-2H-pyrazol-3-ylamine 3. 1H NMR (300 MHz, CDCl3/TMS) δ 7.44-7.35 (m, 3H), 7.30-7.25 (m, 2H), 5.57 (d, J=2.1 Hz, 1H), 3.57 (br s, 2H), 2.49 (q, J=7.6 Hz, 2H), 1.10 (t, J=7.6 Hz, 3H), 13C NMR (75 MHz, CDCl3/TMS) δ 145.20, 142.60, 139.62, 135.93, 129.47, 129.41, 127.88, 126.55, 88.70, 24.04, 14.34.

후처리

  1. temperatureunder reflux for 8 hours
  2. temperaturethe mixture was further heated for 6 hours
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was treated with water (100 mL)
  5. extractionthe product extracted with ethyl acetate (3*100 mL)
  6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-205e46c326904f8fa7bc258c9380ce62
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085585B2

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