Diethyl Ether → 5-Amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carbonitrile

HRID 2406111

Reaktionsgleichung

Reaktionsgleichung von HRID 2406111
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH:10][NH2:11].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C.C(N(CC)CC)C.C(OCC)C>C(O)C>[NH2:20][C:19]1[N:10]([C:4]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:3]=2[CH3:2])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 124050102,6-Dimethylphenylhydrazine hydrochloride

Produkt 1

HCID 121505545-Amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3.0 g (17.3 mmol) of 2,6-dimethylphenylhydrazine hydrochloride are suspended with 2.1 g (17.3 mmol) of ethoxymethylenemalononitrile in 40 ml of ethanol, and 7.3 ml (52.1 mmol) of triethylamine are added. The reaction mixture is heated to reflux for 3 h, during which a clear solution forms. After cooling to room temperature, diethyl ether is added to this. The triethylammonium chloride which precipitates is filtered off. The solvent is removed in vacuo, and the residue is purified by preparative HPLC (YMC gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B). 2.3 g (62% of theory) of the product are obtained as yellow crystals.

Aufarbeitung

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 3 h, during which a clear solution forms
  4. customThe triethylammonium chloride which precipitates
  5. filtrationis filtered off
  6. customThe solvent is removed in vacuo
  7. customthe residue is purified by preparative HPLC (YMC gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B)
  8. custom2.3 g (62% of theory) of the product are obtained as yellow crystals

Quellen und Nachweise

ORD-Eintrag
ord-6eee0d69dcc648408a359c26045562e4
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809348B2

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