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2-Methoxyethanol → 4-(4-Chloro-2-fluoroanilino)-7-(2-methoxyethoxy)-6-nitroquinazoline

HRID 1838538
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1838538
[Na].[CH3:2][O:3][CH2:4][CH2:5][OH:6].Cl.Cl[C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[F:27])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[N+:28]([O-:30])=[O:29]>C(O)(=O)C.O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([O:6][CH2:5][CH2:4][O:3][CH3:2])=[C:10]([N+:28]([O-:30])=[O:29])[CH:11]=3)[N:16]=[CH:15][N:14]=2)=[C:21]([F:27])[CH:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 80192-MethoxyethanolHCID 5360545SodiumHCID 224782507-Chloro-4-(4-chloro-2-fluoroanilino)-6-nitroquinazoline hydrochloride

Produkt 1

HCID 187534234-(4-Chloro-2-fluoroanilino)-7-(2-methoxyethoxy)-6-nitroquinazolineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium (148 mg, 6.4 mmol) was added to 2-methoxyethanol (10 ml), the mixture stirred for 15 minutes to give a complete solution and the volatiles removed by evaporation. The residue was dissolved in DMSO (5 ml) and 7-chloro-4-(4-chloro-2-fluoroanilino)-6-nitroquinazoline hydrochloride (500 mg, 1.3 mmol) was added. The mixture was stirred at ambient temperature for 18 hours then diluted with a solution of acetic acid (1 ml) in water (20 ml). The resulting precipitate was collected by filtration, washed with water, dried and purified by column chromatography eluting with methylene chloride/methanol (96/4). The purified product was recrystallised from methylene chloride/isohexane to give 4-(4-chloro-2-fluoroanilino)-7-(2-methoxyethoxy)-6-nitroquinazoline (304 mg, 60%) as a yellow solid.

Aufarbeitung

  1. customto give a complete solution
  2. customthe volatiles removed by evaporation
  3. dissolutionThe residue was dissolved in DMSO (5 ml)
  4. stirringThe mixture was stirred at ambient temperature for 18 hours
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried
  8. custompurified by column chromatography
  9. washeluting with methylene chloride/methanol (96/4)
  10. customThe purified product was recrystallised from methylene chloride/isohexane

Quellen und Nachweise

ORD-Eintrag
ord-a0f60cb3763b4b51bad4b44387df5c47
Quelldatensatz
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06673803B2

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