Chloroformamidinium chloride → 2,4-Diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazoline

HRID 363775

Reaktionsgleichung

Reaktionsgleichung von HRID 363775
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[C:6]([CH3:22])[C:3]=1[C:4]#[N:5].[ClH:23].Cl[C:25]([NH2:27])=[NH:26]>COCCOCCOC.C(OCC)C>[NH2:27][C:25]1[N:26]=[C:4]([NH2:5])[C:3]2[C:2](=[CH:9][CH:8]=[C:7]([C:10]([Cl:23])=[CH:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=3)[C:6]=2[CH3:22])[N:1]=1

Komponenten

5

Edukt 2

HCID 3084509Chloroformamidinium chlorideHCID 541158512-Amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile

Produkt 1

HCID 537897802,4-Diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazolineAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8150DiglymeLösungsmittel

Versuchsvorschrift

This compound was prepared in a manner analogous to that of Step E of Example 1, using 2.7 grams (0.009 mole) of 2-amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile and 1.2 grams (0.011 mole) of chloroformamidine hydrochloride in 10 mL of 2-methoxyethyl ether. Upon completion of the reaction, the reaction mixture was diluted with 200 mL of diethyl ether. The resultant solid was collected by filtration, and was dissolved in a hot mixture of 300 mL of water and 100 mL of n-propanol. The solution was filtered hot through a sintered glass funnel to remove some insoluble material. The filtrate was then made basic with 100 mL of concentrated ammonium hydroxide. The resultant solid was collected by filtration, and dried at 60° C. under vacuum. The solid was then dissolved in a solution of 10% methanol in methylene chloride, and the solution was subjected to column chromatography on silica gel. Elution was accomplished using 10% methanol in methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 1.6 grams of 2,4-diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazoline, mp >300° C. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. customThis compound was prepared in a manner analogous to that of Step E of Example 1
  2. customUpon completion of the reaction
  3. filtrationThe resultant solid was collected by filtration
  4. dissolutionwas dissolved in a hot mixture of 300 mL of water and 100 mL of n-propanol
  5. filtrationThe solution was filtered hot through a sintered glass funnel
  6. customto remove some insoluble material
  7. filtrationThe resultant solid was collected by filtration
  8. customdried at 60° C. under vacuum
  9. dissolutionThe solid was then dissolved in a solution of 10% methanol in methylene chloride
  10. washElution
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f5a5a7a2eaa24d90be44ac378bc0424c
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874579

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