Dimethylcarbamoyl Chloride → 3-(N,N-dimethylcarbamoyl)-2-isopropylpyrazolo[1,5-a]pyridine

HRID 436810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 436810
[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[CH3:13][N:14]([CH3:18])[C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:13][N:14]([CH3:18])[C:15]([C:12]1[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12)=[O:16]

Komponenten

5

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Produkt 1

HCID 203220123-(N,N-dimethylcarbamoyl)-2-isopropylpyrazolo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

A mixture of 1.6g of 2-isopropylpyrazolo[1,5-a]pyridine and 2.1g of N,N-dimethylcarbamoyl chloride was dissolved in 20 ml of nitrobenzene. Four grams of aluminum chloride (powder) was added at room-temperature to the resulting solution and reaction mixture was refluxed for 8 hr and concentrated under reduced pressure. Water was added to the residue and the mixture was made basic with potassium hydroxide solution, extracted with chloroform. The chloroform solution was dried over sodium sulfate and concentrated. The residue was column chromatographed over aluminum to give objective product. Distillation gave colorless oil, bp 175° (2 mmHg). Yield 1.1g (50%).

Aufarbeitung

  1. temperaturewas refluxed for 8 hr
  2. concentrationconcentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform solution was dried over sodium sulfate
  6. concentrationconcentrated
  7. customchromatographed over aluminum
  8. customto give objective product
  9. distillationDistillation
  10. customgave colorless oil, bp 175° (2 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-0e64a6d06eec48d2a08406aced2fff0b
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04028370

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