Dimethylformamide → 1-[5-Methyl-2-(4-pyridinyl)-1H-imidazol-4-yl]ethanone

HRID 569463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 569463
[CH3:1][C:2](=[O:8])[C:3](=O)[C:4](=O)[CH3:5].[N:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=1.C[N:18](C)C=O>>[CH3:5][C:4]1[NH:18][C:15]([C:12]2[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=2)=[N:16][C:3]=1[C:2](=[O:8])[CH3:1]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 773174-PyridinemethanamineHCID 1367032,3,4-Pentanetrione

Produkt 1

HCID 133879391-[5-Methyl-2-(4-pyridinyl)-1H-imidazol-4-yl]ethanone

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A mixture of 6.5 g of 2,3,4-pentanetrione, 3-oxime and 6.0 g of 4-pyridylmethylamine in 75 ml of N,N-dimethylformamide was stirred at reflux temperature for 4 hours, then the solvent was removed in vacuo and 100 ml of acetonitrile was added to the residual oil. This mixture was boiled, then cooled at -10° C. The resulting precipitate was collected, washed with 50 ml of cold acetonitrile, air dried and then recrystallized from 150 ml of boiling acetonitrile after treatment with activated charcoal by cooling at -10° C., giving 4.0 g of the desired compound as a tan solid, mp 181°-183° C.

Aufarbeitung

  1. temperatureat reflux temperature for 4 hours
  2. customthe solvent was removed in vacuo and 100 ml of acetonitrile
  3. additionwas added to the residual oil
  4. customThe resulting precipitate was collected
  5. washwashed with 50 ml of cold acetonitrile, air
  6. customdried
  7. customrecrystallized from 150 ml of boiling acetonitrile after treatment with activated charcoal
  8. temperatureby cooling at -10° C.

Quellen und Nachweise

ORD-Eintrag
ord-f234247d74af4d31a6375ecca0383c2b
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04732895

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