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

HRID 224686

반응식

HRID 224686 반응식
[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

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 178508668HCID 178508668, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-df578b050ffb4b51becb18539791bf19
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04233445

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