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

HRID 1706788

反応式

HRID 1706788 の反応式
[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

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 178508668HCID 178508668、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bb1bcc0458484207a6b416121140ae08
出典データセット
uspto-grants-1980_06
特許番号
US04208520

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