Methane, dichloromethoxy- → HCID 178418995, Verbindung

HRID 10699

Reaktionsgleichung

Reaktionsgleichung von HRID 10699
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[NH:19][C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[N:12]=1.[CH3:20][O:21]C(Cl)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[N:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[NH:19][C:11]=1[C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[C:6]([CH:5]=1)[CH:20]=[O:21]

Komponenten

5

Edukt 2

HCID 21004Methane, dichloromethoxy-HCID 178419000HCID 178419000, Verbindung

Produkt 1

HCID 178418995HCID 178418995, VerbindungAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ex-76B: To a suspension of 2-(2,4-dimethoxy-phenyl)-3H-imidazo[4,5-b]pyridine (0.44 g, 1.7 mmol) in 20 ml of CH2Cl2, 1,1-dichlorodimethyl ether (0.55 g, 4.8 mmol) was added. The mixture was cooled to 0° C. with a water-ice bath, and 7 ml (7 mmol) of TiCl4 (1.0 m in CH2Cl2) was added dropwise. The mixture was stirred at 0° C. for 2 hrs, then room temperature for overnight. The reaction mixture was poured into ice-water and the precipitate was filtered to give 0.31 g (63%) of 5-(3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethoxy-benzaldehyde as a white solid. 1H-NMR (DMSO-d6) δ 10.22 (s, 1H), 8.67 (s, 1H), 8.56 (d, J=5 Hz, 1H), 8.44 (d, J=8 Hz, 1H), 7.57–7.61 (m, 1H), 6.97 (s, 1H), 4.19 (s, 3H), 4.06 (s, 3H). HMRS (EI) calc. for C15H13N3O3: 283.0957; found: 283.0952.

Aufarbeitung

  1. additionwas added
  2. waitroom temperature for overnight
  3. filtrationthe precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-b012cffa1faa47589059e872491db161
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

Verknüpfte Notizen

Wird geladen…