Ammonia → HCID 178442312, Verbindung

HRID 842720

Reaktionsgleichung

Reaktionsgleichung von HRID 842720
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]#[N:8].[C:9]([NH2:16])(=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-:26].[K+].[K+].C([O-])(=O)C.[Na+].BrBr.Cl.N>C(O)(=O)C.O.CN(C=O)C>[CH2:17]([N:3]1[C:4]([OH:26])=[N:5][C:6]2[C:2]1=[N:1][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:16][C:7]=2[NH2:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

12

Edukt 8

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 12332HexanamideHCID 24408BromineHCID 787775-amino-1H-imidazole-4-carbonitrileHCID 517045Sodium Acetate

Produkt 1

HCID 178442312HCID 178442312, VerbindungAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.09 g (11 mmol) of 4-amino-5-cyanoimidazole and 4.39 g (38 mmol) of hexanamide were stirred at 210° C. for 15 hr with heating under an atmosphere of nitrogen. A mixed solvent composed of DMF (200 ml) and water (50 ml) was added thereto. Further, 3.0 ml of benzyl chloride and 3.00 g of potassium carbonate were added thereto. The resultant mixture stirred at 70° C. for 6 hr under heating. After the solvent was removed by vacuum distillation, the residue was taken into water and extracted with dichloromethane. The organic layer was vacuum-concentrated. The residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=100:1-50:1) to thereby obtain a solid. This solid and 5.00 g of sodium acetate were dissolved in 40 ml of acetic acid. Then, 2 ml of bromine was added to the solution placed in ice bath. Subsequently, the resultant solution was stirred at 70° C. for 6 hours under heating. After the solvent was removed by vacuum distillation, the residue was extracted with ethyl acetate, and the organic layer was vacuum-concentrated. The residue was purified by column chromatography (eluent: dichloromethane:methanol=100:1) to obtain a solid. This solid was added to 20 ml of concentrated hydrochloric acid and heated for 6 hours under refluxing. After the reaction solution was cooled, its pH was adjusted to 8 with aqueous ammonia. The deposited solid was vacuum-filtered, washed with water and then dried to thereby obtain 0.25 g of the captioned compound (yield: 8%).

Aufarbeitung

  1. temperaturewith heating under an atmosphere of nitrogen
  2. additionwas added
  3. temperatureunder heating
  4. customAfter the solvent was removed by vacuum distillation
  5. extractionextracted with dichloromethane
  6. concentrationThe organic layer was vacuum-concentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=100:1-50:1)
  8. customto thereby obtain a solid
  9. temperatureunder heating
  10. customAfter the solvent was removed by vacuum distillation
  11. extractionthe residue was extracted with ethyl acetate
  12. concentrationthe organic layer was vacuum-concentrated
  13. customThe residue was purified by column chromatography (eluent: dichloromethane:methanol=100:1)
  14. customto obtain a solid
  15. temperatureheated for 6 hours
  16. temperatureunder refluxing
  17. temperatureAfter the reaction solution was cooled
  18. filtrationThe deposited solid was vacuum-filtered
  19. washwashed with water
  20. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e3d807c0fc6244a5b7e475e17babfe09
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376501B1

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