Triethylamine → 5-Amino-1-(2-ethylphenyl)-1H-pyrazole-4-carbonitrile

HRID 2406113

Reaktionsgleichung

Reaktionsgleichung von HRID 2406113
Cl.[CH2:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][NH2:11])[CH3:3].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C.C(N(CC)CC)C>C(O)C.ClCCl>[NH2:20][C:19]1[N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:2][CH3:3])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 27332092-Ethylphenylhydrazine Hydrochloride

Produkt 1

HCID 121505585-Amino-1-(2-ethylphenyl)-1H-pyrazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 3.0 g (17.0 mmol) of 2-ethylphenylhydrazine hydrochloride and 2.12 g (17.0 mmol) of ethoxymethylenemalononitrile in 36 ml of ethanol is mixed with 7.1 ml (51.1 mmol) of triethylamine and heated at 60° C. until the reaction is complete according to a TLC check (about 30 min). For working up, the solvent is stripped off, and the residue is taken up in dichloromethane, washed with saturated sodium bicarbonate solution and dried over sodium sulphate. Concentration results in a crude product which is purified by column chromatography on silica gel (mobile phase dichloromethane with 0-10% methanol). 3.05 g (83.5% of theory) of the desired product are obtained.

Aufarbeitung

  1. customis complete according to a TLC check (about 30 min)
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationConcentration
  5. customresults in a crude product which
  6. customis purified by column chromatography on silica gel (mobile phase dichloromethane with 0-10% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-72ac73fcbd8a44bc9209e6e6d971e21c
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809348B2

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