Dimethylamine, hydrochloride → N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

HRID 467633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467633
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[C:4]([C:10]([OH:12])=O)=[N:3]1.[CH3:13][N:14](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:15].[B-](F)(F)(F)F.Cl.CNC.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:13][N:14]([CH3:15])[C:10]([C:4]1[C:5]([N+:7]([O-:9])=[O:8])=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:12]

Komponenten

6

Edukt 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 5359761-Methyl-4-nitro-1H-pyrazole-3-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 67076071N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid (500 mg, 2.92 mmol) in DMF (5 ml) under inert gas atmosphere was treated with TBTU (1030 mg, 3.2 mmol), dimethylamine hydrochloride (262 mg, 3.2 mmol) and N,N-diisopropylethylamine (2.0 ml, 11.7 mmol) and stirring was continued for 4 h. All volatiles were removed and the crude product was extracted with water and ethyl acetate. The organic phase was washed with sodium bicarbonate and the aqueous phases were back-extracted with ethyl acetate and dichloromethane. The combined organic phases were dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a dichloromethane/methanol gradient as white solid (230 mg, 40%).

Aufarbeitung

  1. customAll volatiles were removed
  2. extractionthe crude product was extracted with water and ethyl acetate
  3. washThe organic phase was washed with sodium bicarbonate
  4. extractionthe aqueous phases were back-extracted with ethyl acetate and dichloromethane
  5. customThe combined organic phases were dried
  6. customthe solvent was evaporated
  7. customThe product was obtained
  8. customafter purification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-803839c5a5684682adf59b8aa530745e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623866B2

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