Ammonia → 7-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-1-methyl-1H-benzo[d]imidazol-6-amine

HRID 2299126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299126
[CH3:1][N:2]1[C:6]2[C:7]([Br:12])=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[NH3:13]>C(O)C(C)C>[CH3:1][N:2]1[C:6]2[C:7]([Br:12])=[C:8]([NH:11][C:1]3[NH:13][CH2:5][CH2:6][N:2]=3)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 129684523-Methyl-4-bromo-5-aminobenzimidazole

Produkt 1

HCID 129684437-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-1-methyl-1H-benzo[d]imidazol-6-amineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6560IsobutanolLösungsmittel

Versuchsvorschrift

A solution of 3-methyl-4-bromo-5-aminobenzimidazole (0.31 g, 1.4 mmol) and ISA (0.6 g, 4.5 mmol) in 10 ml of isobutanol was stirred at reflux for 12 h. Oily residue obtained was subjected to column chromatography (NH3 sat'd 20% isopropanol/EtOAc) to yield 0.39 g (1.3 mmol, 93%) of the desired product. The product obtained was converted to the fumarate salt and recrystallized from MeOH to afford 0.50 g (68%) of the product as a white solid: mp 209-210° C.; Anal. Calc. for C11H12N5Br.2.0C4H4O4. requires C, 43.36; H, 3.83; N, 13.31. Found: C, 43.66; H, 3.84; N, 13.10.

Aufarbeitung

  1. temperatureat reflux for 12 h
  2. customOily residue obtained

Quellen und Nachweise

ORD-Eintrag
ord-205a7d44484142998104212fa7d928d1
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495583B1

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