1,3-Dimethyl-2-imidazolidinone → HCID 18326386, Verbindung

HRID 1250610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250610
[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].CN1CCN(C)C1=O.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C.[ClH:36].[CH3:37][C:38]([CH3:42])=[CH:39][CH2:40][NH2:41]>O>[Cl:36][C:9]1[N:8]=[C:7]([NH:41][CH2:40][CH:39]=[C:38]([CH3:42])[CH3:37])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Komponenten

7

Edukt 5

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedioneHCID 183265643-Methylbut-2-en-1-amine hydrochloride

Produkt 1

HCID 18326386HCID 18326386, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 278 mg (1.45 mmol) of 6-nitroquinazoline-2,4(1H,3H)-dione were added 0.71 ml of 1,3-dimethyl-2-imidazolidinone and 5.48 g (35.76 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 2.81 ml (20.0 mmol) of triethylamine and 267 mg (2.19 mmol) of 3-methyl-2-butenylamine hydrochloride and stirring under ice cooling for 2 hours. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off to give 2-chloro-4-(3-methyl-2-butenylamino)-6-nitroquinazoline. After 1.00 ml (13.33 mmol) of allylamine was added thereto and then the mixture was stirred at room temperature for 3 hours, water was added to the reaction solution, 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 70 mg (16.7%) of the title compound.

Aufarbeitung

  1. temperatureto heating
  2. temperatureunder reflux for 3 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 3 ml of acetonitrile
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-79f06f174b2140b2af9e3a1b3fdfac68
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339089B2

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