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

HRID 1526480

Reaktionsgleichung

Reaktionsgleichung von HRID 1526480
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 13020083Ethylenediaminetetraacetic acid disodium saltKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-205e46c326904f8fa7bc258c9380ce62
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085585B2

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