Triethylamine → 3-tert-Butyl-1-(3,4-dimethylphenyl)-1H-pyrazol-5-amine

HRID 594201

Reaktionsgleichung

Reaktionsgleichung von HRID 594201
[C:1]([CH2:7][C:8]#[N:9])(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].Cl.[CH3:11][C:12]1[CH:13]=[C:14]([NH:19][NH2:20])[CH:15]=[CH:16][C:17]=1[CH3:18].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:2]([C:1]1[CH:7]=[C:8]([NH2:9])[N:19]([C:14]2[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([CH3:11])[CH:13]=2)[N:20]=1)([CH3:5])([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 1737401-(3,4-Dimethylphenyl)hydrazine hydrochlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 108685003-tert-Butyl-1-(3,4-dimethylphenyl)-1H-pyrazol-5-amineAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of pivaloylacetonitrile (400 mg) in toluene (10 mL) were added 3,4-dimethylphenylhydrazine hydrochloride (520 mg) and triethylamine (0.4 mL) and refluxed with heating for 5 hours. The reaction mixture was added with a saturated sodium hydrogen carbonate aqueous solution. The obtained organic layer was washed with a saturated sodium chloride aqueous solution. The obtained organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=4:1) to give the titled compound (490 mg) having the following physical data.

Aufarbeitung

  1. temperaturerefluxed
  2. temperaturewith heating for 5 hours
  3. washThe obtained organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-c103ebe0bf7f4f7eb4213ff3e0bbd809
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242977B2

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