Water → HCID 57500678, Verbindung

HRID 1919657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919657
O=[C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[NH:3]1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:30].O>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:30][C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[N:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 57500672HCID 57500672, Verbindung

Produkt 1

HCID 57500678HCID 57500678, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Methyl 4-oxo-4,5-dihydrothiazolo[4,5-c]quinoline-7-carboxylate (1.0 eq, 0.62 g, 2.38 mmol) was suspended in toluene. DIEA (1.5 eq, 122 ul, 3.57 mmol) and POCl3 (2.3 eq, 507 ul, 5.47 mmol) were added and the mixture vigorously stirred at 120° C. for 1 hour. Water, ice and CH2Cl2 were added and the resulting emulsion filtered through celite. The organic phase was decanted and the aqueous phase further extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4 and the solvent removed in vacuo to afford methyl 4-chlorothiazolo[4,5-c]quinoline-7-carboxylate (0.31 g, 47% yield). LCMS (ES): >90% pure, m/z 279[M+1]+.

Aufarbeitung

  1. filtrationthe resulting emulsion filtered through celite
  2. customThe organic phase was decanted
  3. extractionthe aqueous phase further extracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6e052a93807f4c69b38e8fcbc95c7fe3
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168651B2

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