Dimethylformamide → 7-[(2,4-Dichlorophenyl)methyl]pyrrolo[3,2-f]quinazoline-1,3-diamine

HRID 224686

Reaktionsgleichung

Reaktionsgleichung von HRID 224686
[C:1]1([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=[C:5]2[C:10]=1[C:9]1[CH:11]=[CH:12][NH:13][C:8]=1[CH:7]=[CH:6]2.CN(C)C=O.[H-].[Na+].[Cl:23][C:24]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:25]=1[CH2:26]Cl>C(O)(=O)C>[Cl:23][C:24]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:25]=1[CH2:26][N:13]1[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[C:1]([NH2:15])[N:2]=[C:3]([NH2:14])[N:4]=3)[C:9]=2[CH:11]=[CH:12]1

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 178508668HCID 178508668, Verbindung

Produkt 1

HCID 4858507-[(2,4-Dichlorophenyl)methyl]pyrrolo[3,2-f]quinazoline-1,3-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A suspension of 7.97 g. of 7-H-pyrrolo[3,2-f]quinazoline-1,3-diamine in 500 ml. of dry dimethylformamide is stirred under nitrogen as 4.61 g. of ca. 50% sodium hydride-mineral oil dispersion is added carefully. After stirring for 1.5 hours, a solution of 8.99 g. of 2,4-dichlorobenzyl chloride in 30 ml. of dry dimethylformamide is added during ca. 10 minutes. Stirring is continued for 5 hours and then 25 ml. of glacial acetic acid is added to the reaction mixture. After removal of solvent (in vacuo), the residue is stirred throughly with a mixture of excess aqueous potassium carbonate solution and 100 ml. of 1 N sodium hydroxide solution and filtered. The crude product is dissolved in 5 liters of boiling methanol, treated with charcoal, and filtered through Celite. The filtrate is concentrated to ca. 500 ml. and chilled. The crystalline solid is collected and again recrystallized from methanol to afford 6.33 g. of the title compound, m.p. 249°-250° C., NMR (dDMSO and D2O): δ 5.58 (singlet, N--CH2 --C6H3Cl2), 6.68 (doublet, J=8 Hz, 5H), 7.10 (doublet, J=3 Hz, 9H), 7.52 (doublet, J=3 Hz, 8H), 7.68 (doublet, J=8 Hz, 6H) p.p.m.; λmax95%EtOH 258 mμ (26,000) and 315 mμ (8,500).

Aufarbeitung

  1. additionA suspension of 7.97 g
  2. stirringStirring
  3. waitis continued for 5 hours
  4. customAfter removal of solvent (in vacuo)
  5. stirringthe residue is stirred throughly with a mixture of excess aqueous potassium carbonate solution and 100 ml
  6. filtrationof 1 N sodium hydroxide solution and filtered
  7. dissolutionThe crude product is dissolved in 5 liters of boiling methanol
  8. additiontreated with charcoal
  9. filtrationfiltered through Celite
  10. concentrationThe filtrate is concentrated to ca. 500 ml
  11. temperatureand chilled
  12. customThe crystalline solid is collected
  13. customagain recrystallized from methanol
  14. customto afford 6.33 g

Quellen und Nachweise

ORD-Eintrag
ord-df578b050ffb4b51becb18539791bf19
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04233445

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