Toluene → HCID 178478309, Verbindung

HRID 520274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520274
C1(C)C=CC=CC=1.P(Cl)(Cl)([Cl:10])=O.[NH:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:18]([O-])=[CH:17][C:16]=2[N:15]=[CH:14]1>CN(C)C=O>[Cl:10][C:17]1[C:16]2[N:15]=[CH:14][NH:13][C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 178526229HCID 178526229, Verbindung

Produkt 1

HCID 178478309HCID 178478309, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of toluene (0.45 ml/mmol) and dimethylformamide (0.90 ml/mmol) was cooled in an ice-bath and phosphorus oxychloride (2.6 eq.) was added. After 10 minutes the appropriate 1H-imidazo[4,5-c]quinolin-5-oxide was added and the solution was stirred at room temperature for 10 minutes. Subsequently the solution was heated to 100° C. on a steam bath for 30 minutes. Upon cooling, the solvent was evaporated and the resulting syrup was poured over crushed ice while stirring. The mixture was then warmed to room temperature and carefully adjusted to pH 6-7 with solid NaHCO3. After 2 hours, the solid that was formed was filtered off, washed with water and diisopropylether and subsequently dried.

Aufarbeitung

  1. temperaturewas cooled in an ice-bath
  2. temperatureSubsequently the solution was heated to 100° C. on a steam bath for 30 minutes
  3. temperatureUpon cooling
  4. customthe solvent was evaporated
  5. additionthe resulting syrup was poured
  6. customover crushed ice
  7. stirringwhile stirring
  8. temperatureThe mixture was then warmed to room temperature
  9. waitAfter 2 hours
  10. customthe solid that was formed
  11. filtrationwas filtered off
  12. washwashed with water and diisopropylether
  13. customsubsequently dried

Quellen und Nachweise

ORD-Eintrag
ord-bfb158df51b8473bb4e99547ee03ddf0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326978B2

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