Ammonia → 5-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamide

HRID 2406114

Reaktionsgleichung

Reaktionsgleichung von HRID 2406114
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:14])[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[OH:17]O.N>C(O)C.ClCCl>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:14])[N:5]=[CH:4][C:3]=1[C:15]([NH2:16])=[O:17]

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 121505545-Amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carbonitrile

Produkt 1

HCID 121505615-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2 g (9.4 mmol) of 5-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carbonitrile (Example 1A) are dissolved in 25 ml of ethanol, and a mixture of 20 ml of 30% strength hydrogen peroxide and 40 ml of 25% strength ammonia is added. The solution is stirred at room temperature overnight and then concentrated to about 15 ml in a rotary evaporator. The oily emulsion resulting thereby is taken up in dichloromethane. It is washed several times with water and saturated sodium thiosulphate solution. Drying over magnesium sulphate is followed by removal of the solvent in vacuo. 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). 0.88 g (40% of theory) of the product is obtained as colourless solid.

Aufarbeitung

  1. additionis added
  2. concentrationconcentrated to about 15 ml in a rotary evaporator
  3. customThe oily emulsion resulting
  4. washIt is washed several times with water and saturated sodium thiosulphate solution
  5. dry with materialDrying over magnesium sulphate
  6. customis followed by removal of the solvent 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. custom0.88 g (40% of theory) of the product is obtained as colourless solid

Quellen und Nachweise

ORD-Eintrag
ord-b70d72d0679b414e8e11547f6923af31
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809348B2

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