Cyclohexylhydrazine hydrochloride → 5-Amino-1-cyclohexyl-1H-pyrazole-4-carbonitrile

HRID 1804530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804530
Cl.[CH:2]1([NH:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C[O-].[Na+].C(O[CH2:16][CH:17]([C:20]#[N:21])[C:18]#[N:19])C>C(O)C>[NH2:21][C:20]1[N:8]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[N:9]=[CH:16][C:17]=1[C:18]#[N:19]

Komponenten

5

Edukt 3

HCID 207836Cyclohexylhydrazine hydrochlorideHCID 296281Ethoxymethyl malononitrileHCID 10942334Sodium Methoxide

Produkt 1

HCID 6900055-Amino-1-cyclohexyl-1H-pyrazole-4-carbonitrileAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To cyclohexylhydrazine hydrochloride (7.52 g, 50 mmol) generated above in 500 mL absolute ethanol was added sodium methoxide (Aldrich, 2.7 g, 50 mmol). The mixture was stirred briefly and ethoxymethylmalononitrile (Acros, 6.11 g, 50 mmol) was added in small portions over twenty minutes. The reaction mixture was then heated at 70° C. under argon overnight. On cooling, the reaction was concentrated and subjected to flash chromatography on silica gel (1:1 hexane:ethyl acetate) affording 6.3 g (66%) of a light brown solid. Compound 8: mp 99-103° C.; MS (ES+ calculated: 190.25; found: 191.15 M+H). HPLC (97% purity, retention time 11.135 minutes—Method A); 1H NMR (400 MHz, DMSO-d6) δ 7.50 (s, 1H), 6.49 (br s, 2H), 4.02 (m, 1H), 1.80-1.10 (m, 10H).

Aufarbeitung

  1. temperatureOn cooling
  2. concentrationthe reaction was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-70ebde533aa54cb193a83f9d51a86d82
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354414B2

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