Diisopropylethylamine → 4,5-Dichloropyrrolo[2,1-f][1,2,4]triazine

HRID 2117124

Reaktionsgleichung

Reaktionsgleichung von HRID 2117124
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=O)[NH:8][CH:7]=[N:6]2.C(N(C(C)C)CC)(C)C.O(Cl)[Cl:22].[P+3].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:22][C:9]1[C:10]2=[C:2]([Cl:1])[CH:3]=[CH:4][N:5]2[N:6]=[CH:7][N:8]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 1357420865-Chloropyrrolo[2,1-f][1,2,4]triazin-4(1H)-oneHCID 178479710HCID 178479710, Verbindung

Produkt 1

HCID 210816694,5-Dichloropyrrolo[2,1-f][1,2,4]triazineAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 5-chloropyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (5.00 g, 29.5 mmol) in toluene (100 mL) at rt under nitrogen was added diisopropylethylamine (5.14 mL, 29.5 mmol) followed by phosphorus(III) oxychloride (8.25 mL, 88.5 mmol). The mixture was heated at 100° C. for 20 h and was then cooled to rt. The reaction was slowly added to saturated aqueous sodium bicarbonate solution (500 mL) at 0° C. After the addition was complete, the mixture was stirred at rt for 30 min. The aqueous phase was extracted with ethyl acetate (3×500 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give the crude product (3.73 g, 67%) as a yellow solid which was used without further purification. 1H NMR (CDCl3) δ 8.03 (s, 1H), 7.70 (d, 1H, J=2.8 Hz), 6.84 (d, 1H, J=2.8 Hz); MS(ESI+) m/z 188.1 (M+H)+.

Aufarbeitung

  1. temperaturewas then cooled to rt
  2. additionAfter the addition
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×500 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eef68dead9064969a4b2d1a50ede38cd
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439246B2

Verknüpfte Notizen

Wird geladen…