2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → ethyl 5-amino-1-cyclohexyl-1H-pyrazole-4-carboxylate

HRID 1693493

Reaktionsgleichung

Reaktionsgleichung von HRID 1693493
Cl.[CH:2]1([NH:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:10]([O:12][C:13](=[O:21])[C:14]([C:19]#[N:20])=[CH:15]OCC)[CH3:11].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[CH:15]=[N:9][N:8]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[C:19]=1[NH2:20])=[O:21])[CH3:11]

Komponenten

5

Edukt 3

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 207836Cyclohexylhydrazine hydrochlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 351028ethyl 5-amino-1-cyclohexyl-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a round bottom flask is added cyclohexyl-hydrazine hydrochloride (4.5 g, 30 mmol), 2-cyano-3-ethoxy-acrylic acid ethyl ester (5.1 g, 30 mmol), sodium bicarbonate (2.6 g, 30.9 mmol) and 40 mL of ethanol. The mixture is heated to 80° C. for 1 hour, cooled down to room temperature and concentrated. The residue is dissolved in chloroform and washed with water, dried over sodium sulfate. After removal of the solvent, the solid is recrystallized from ethyl acetate: 1HNMR (CDCl3): δ 7.40 (1 H, s), 4.77 (2 H, brs), 4.05 (2 H, q, J=7.2 Hz), 3.50 (1 H, m), 1.61-1.71 (6 H, m), 1.50 (1 H, m), 1.02-1.21 (3 H, m), 1.13 (3 H, t, J=7.2 Hz).

Aufarbeitung

  1. temperaturecooled down to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent
  7. customthe solid is recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-07328134611a46d4b3c645e6659a2193
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158634B2

Verknüpfte Notizen

Wird geladen…