2-Chloroethyl methyl sulfide → 6-Methoxy-7-(2-methylthioethoxy)4-phenoxyquinazoline

HRID 634695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634695
[CH3:1][S:2][CH2:3][CH2:4]Cl.[OH:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[O:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:25][O:24][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:7]=1[O:6][CH2:4][CH2:3][S:2][CH3:1])[N:14]=[CH:13][N:12]=[C:11]2[O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 109652-Chloroethyl methyl sulfideHCID 11430Potassium CarbonateHCID 1354961377-Hydroxy-6-methoxy-4-phenoxyquinazoline

Produkt 1

HCID 212602746-Methoxy-7-(2-methylthioethoxy)4-phenoxyquinazolineAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2-Chloroethyl methyl sulphide (1.2 g, 10.9 mmol) was added to 7-hydroxy-6-methoxy-4-phenoxyquinazoline (2.25 g, 8.4 mmol), (prepared as described for the starting material in Example 16), and potassium carbonate (6.0 g, 43.4 mmol) in DMF (70 ml). The mixture was heated at 110° C. for 4 hours and allowed to cool. The mixture was filtered, and the volatiles were removed from the filtrate by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (96/4) to give 6-methoxy-7-(2-methylthioethoxy)4-phenoxyquinazoline (1.55 g, 54%).

Aufarbeitung

  1. custom(prepared
  2. temperatureto cool
  3. filtrationThe mixture was filtered
  4. customthe volatiles were removed from the filtrate by evaporation
  5. customThe residue was purified by column chromatography
  6. washeluting with methylene chloride/methanol (96/4)

Quellen und Nachweise

ORD-Eintrag
ord-74b387d7a47b4748b60276a6261487fe
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184225B2

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