Aminoacetaldehyde dimethyl acetal → 7,10-Di-tert-butyl-imidazo[1,2-f]phenanthridine

HRID 924569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924569
[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]3[C:13](=[C:14](Cl)[N:15]=2)[CH:12]=[CH:11][C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9]3)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO[CH:26](OC)[CH2:27][NH2:28]>COCCOCCOC>[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[N:15]3[CH:26]=[CH:27][N:28]=[C:14]3[C:13]3[CH:12]=[CH:11][C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][C:8]=3[C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 574376592,9-Di-tert-butyl-6-chlorophenanthridine

Produkt 1

HCID 581623657,10-Di-tert-butyl-imidazo[1,2-f]phenanthridineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

2,9-Di-t-butyl-6-chlorophenanthridine (3.7 grams, 11.0 mmole) was added to a reaction flask containing aminoacetaldehyde dimethylacetal (2.4 grams, 23 mmole) dissolved into 200 mL of diglyme, heated to reflux and stirred under a nitrogen atmosphere. After 96 hours the reaction was complete as determined by TLC. The reaction mixture was cooled to room temperature and the excess solvent removed by distillation. The residue was taken up into methylene chloride. The solvent was dried over magnesium sulfate filtered and concentrated. The crude product was purified by silica gel chromatography using 10% ethyl acetate and 90% methylene chloride as the eluents. The purified product was collected, washed with hexanes, and dried to give 7,10-di-tert-butyl-imidazo[1,2-f]phenanthridine (2.0 grams, 56% yield) as a white solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux
  3. customthe excess solvent removed by distillation
  4. dry with materialThe solvent was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography
  8. customThe purified product was collected
  9. washwashed with hexanes
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d4d73739ce1b4d2f853037f0f6ce0e50
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09281483B2

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