Phosphorus oxychloride → 4-Chloro-7-(3-chloropropoxy)-6-methoxyquinazoline

HRID 631257

Reaktionsgleichung

Reaktionsgleichung von HRID 631257
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](O)=[N:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:17][CH3:18].P(Cl)(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][C:10]1[C:9]2[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[C:7]([O:17][CH3:18])[CH:8]=2)[N:13]=[CH:12][N:11]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 1784867697-(3-chloropropoxy)-6-methoxy-1H-quinazolin-4-one

Produkt 1

HCID 574472274-Chloro-7-(3-chloropropoxy)-6-methoxyquinazolineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

To a solution of the intermediate from Step 4 (3.00 g, 11.16 mmol) in toluene (30 mL) in a pressure vessel was added phosphorous oxychloride (8 mL). The mixture was heated to 125° C. for 5 hours. Completion of the reaction was monitored by LCMS. The mixture was concentrated to dryness and excess ethyl acetate was added. The solution was washed with water and brine and was dried (Na2SO4) and concentrated to afford the pure compound 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinazoline (2.51 g, 78%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.85 (s, 1H), 7.48 (s, 1H), 7.35 (s, 1H), 4.35 (t, 2H), 4.00 (s, 3H), 3.75 (t, 2H), 2.25 (q, 2H). LC-MS (ESI)m/z 287 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness and excess ethyl acetate
  2. additionwas added
  3. washThe solution was washed with water and brine
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bd76335f28a84b6c96c4d33b08f4f83e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320739B2

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