Triethylamine → N,N,1-trimethyl-1H-pyrazole-4-carboxamide

HRID 1802271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802271
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3]1.[CH2:10]([N:12](CC)[CH2:13]C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.CNC>CN(C=O)C>[CH3:10][N:12]([CH3:13])[C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:9]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 6431601-Methyl-1H-pyrazole-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 59551573N,N,1-trimethyl-1H-pyrazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl-1H-pyrazole-4-carboxylic acid (1.0 g, 7.93 mmol) was combined with DMF (10.0 ml) to give a light yellow solution. Triethylamine (3.3 ml, 23.8 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (2.8 g, 8.72 mmol) were added. The reaction mixture was set under argon and stirred for 1 h at RT. Then dimethylamine hydrochloride (679 mg, 8.33 mmol) was added. The reaction mixture was stirred over night. The solvent was evaporated and the residue was absorbed on silica gel and chromatographed (amine silica gel cartridge, CH2Cl2). The resulting brown oil was dried at the HV over night. Yield: 1.16 g (96%); brown oil; MS: m/z=154.1 [M+H]+.

Aufarbeitung

  1. customto give a light yellow solution
  2. stirringThe reaction mixture was stirred over night
  3. customThe solvent was evaporated
  4. customthe residue was absorbed on silica gel
  5. customchromatographed (amine silica gel cartridge, CH2Cl2)
  6. customThe resulting brown oil was dried at the HV over night

Quellen und Nachweise

ORD-Eintrag
ord-7052bce9aa1e439ca487024c77df2979
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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