Ethylamine → 2-Allylamino-4-ethylamino-6-nitroquinazoline

HRID 1250573

Reaktionsgleichung

Reaktionsgleichung von HRID 1250573
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.[CH2:21]([NH2:23])[CH3:22].[CH2:24]([NH2:27])[CH:25]=[CH2:26]>O>[CH2:24]([NH:27][C:9]1[N:8]=[C:7]([NH:23][CH2:21][CH3:22])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1)[CH:25]=[CH2:26]

Komponenten

6

Edukt 4

HCID 6341EthylamineHCID 7853AllylamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Produkt 1

HCID 183265292-Allylamino-4-ethylamino-6-nitroquinazolineAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To 311 mg (1.50 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione was added 12.80 g (83.47 mmol) of phosphorus oxychloride to effect reaction in the same manner as in Example 10. Next, to the reaction mixture was added dropwise 151 mg (3.00 mmol) of a 70% aqueous ethylamine solution under ice cooling, and the resulting mixture was stirred under ice cooling for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. The solvent was distilled off to obtain 2-chloro-4-ethylamino-6-niroquinazoline. To the compound thus obtained was added 761 mg (13.33 mmol) of allylamine, and the resulting mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 180 mg (yield: 44.1%) of the title compound.

Aufarbeitung

  1. customreaction in the same manner as in Example 10
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with brine
  4. dry with materialdrying over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customto obtain 2-chloro-4-ethylamino-6-niroquinazoline
  7. customTo the compound thus obtained
  8. stirringthe resulting mixture was stirred at room temperature for 3 hours
  9. extractionfollowed by extraction with ethyl acetate
  10. washwashing with brine
  11. dry with materialdrying over anhydrous sodium sulfate
  12. distillationAfter the solvent was distilled off
  13. customthe residue was purified by a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-ae208f9791db438fa2908c1b2bdddd64
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339089B2

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