Triethylamine → 5-Amino-1-cyclohexyl-1H-pyrazole-4-carbonitrile

HRID 400489

Reaktionsgleichung

Reaktionsgleichung von HRID 400489
C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.C(N(CC)CC)C.Cl.[CH:18]1([NH:24][NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[NH2:9][C:8]1[N:24]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:25]=[CH:4][C:5]=1[C:6]#[N:7]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 207836Cyclohexylhydrazine hydrochloride

Produkt 1

HCID 6900055-Amino-1-cyclohexyl-1H-pyrazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

First ethoxymethylenemalononitrile (2.43 g, 19.9 mmol) and then 8 ml of triethylamine are added to a solution of cyclohexylhydrazine hydrochloride (3 g, 19.9 mmol) in 36 ml of ethanol at room temperature. The mixture is refluxed for 20 min and then cooled. The solvent is stripped off in a rotary evaporator, and the residue is taken up in DCM, washed with aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product is chromatographed on silica gel (mobile phase: dichloromethane/methanol 0-10%).

Aufarbeitung

  1. temperatureThe mixture is refluxed for 20 min
  2. temperaturecooled
  3. customThe solvent is stripped off in a rotary evaporator
  4. washwashed with aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is chromatographed on silica gel (mobile phase: dichloromethane/methanol 0-10%)

Quellen und Nachweise

ORD-Eintrag
ord-b8b80f04833748f58fbc7a0ade4d0bef
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741907B2

Verknüpfte Notizen

Wird geladen…