Hydrochloric Acid → 1-(2-Aminoethyl)-4,5-diphenylimidazole

HRID 362896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362896
O.NN.C1(=O)[N:8]([CH2:9][CH2:10][N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:13]=[CH:12]2)C(=O)C2=CC=CC=C12.Cl>CO>[NH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:13]=[CH:12]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 539687861-(2-Phthalimidoethyl)-4,5-diphenylimidazole

Produkt 1

HCID 540605101-(2-Aminoethyl)-4,5-diphenylimidazoleAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Step 3): 80% Hydrazine monohydrate (0.062 ml, 1.3 mmol) was added to a solution of 1-(2-phthalimidoethyl)-4,5-diphenylimidazole (0.32 g, 0.8 mmol) in methanol (20 ml) under refluxing. The reaction mixture was refluxed for 1 hour, then cooled. The mixture was made acidic slightly with 6N HCl and then filtered to remove phthalhydrazide. The filtrate was concentrated and then the residue was suspended in 2N NaOH. The suspended mixture was extracted with chloroform. The organic layer was washed with brine, dried (MgSO4) and concentrated. The precipitates were recrystallized (ethyl acetate/hexane) to give 1-(2-aminoethyl)-4,5-diphenylimidazole (88.1%): mp 96°-98° C.

Aufarbeitung

  1. temperatureunder refluxing
  2. temperatureThe reaction mixture was refluxed for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove phthalhydrazide
  6. concentrationThe filtrate was concentrated
  7. extractionThe suspended mixture was extracted with chloroform
  8. washThe organic layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe precipitates were recrystallized (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c315d63eb0ae4df4929d670e9e9e8ac0
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872115

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