Benzylamine → 2-Chloro-4-benzylamino-6-nitroquinazoline

HRID 1250564

Reaktionsgleichung

Reaktionsgleichung von HRID 1250564
[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:18])=O.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[Cl:18][C:9]1[N:8]=[C:7]([NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Produkt 1

HCID 183265332-Chloro-4-benzylamino-6-nitroquinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 367 mg (1.77 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione was added 15.13 g (98.70 mmol) of phosphorus oxychloride to effect reaction in the same manner as in Example 10. Next, to the reaction mixture was added dropwise 379 mg (3.54 mmol) of benzylamine under ice cooling, and the resulting mixture was stirred under ice cooling for 2 hours. Water was added to the reaction mixture, and crystals thus precipitated were filtered out to obtain 2-chloro-4-benzylamino-6-nitroquinazoline. To this was added 761 mg (13.33 mmol) of allylamine, and the resulting mixture was stirred at room temperature for 2.5 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 224 mg (yield: 56.8%) of the title compound.

Aufarbeitung

  1. customreaction in the same manner as in Example 10
  2. customthus precipitated
  3. filtrationwere filtered out

Quellen und Nachweise

ORD-Eintrag
ord-141652116b1644c7a1ce2bea9d19db00
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339089B2

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