2-Aminobenzimidazole → 2-(3-Nitrophenyl)benzo[4,5]imidazo[1,2-a]pyrimidine

HRID 2361495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361495
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:10].CN(C)/[CH:13]=[CH:14]/[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)=O>CC(O)=O>[N+:23]([C:19]1[CH:18]=[C:17]([C:15]2[CH:14]=[CH:13][N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[C:2]3[N:10]=2)[CH:22]=[CH:21][CH:20]=1)([O-:25])=[O:24]

Komponenten

4

Edukt 2

HCID 136242-AminobenzimidazoleHCID 5375681(2E)-3-(dimethylamino)-1-(3-nitrophenyl)prop-2-en-1-one

Produkt 1

HCID 583623632-(3-Nitrophenyl)benzo[4,5]imidazo[1,2-a]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a round bottomed flask equipped with a magnetic stir bar, containing AcOH (20 mL) was placed 1H-benzoimidazol-2-amine (1 g, 7.5 mmol, 1.0 equiv). To this solution was added (E)-3-(dimethylamino)-1-(3-nitrophenyl)prop-2-en-1-one (1.7 g, 7.5 mmol, 1 equiv) and the reaction was allowed to stir at 120° C. for 24 h. After the reaction was complete by LCMS, the solvent was completely evaporated and the reaction mixture was neutralized with NaHCO3 solution. Yellow solid was filtered and washed with DCM to give the nitro compound DHK-7-16 0.83 g (39%). MS (ESI, Pos.) m/z: 291.1 M+H]+.

Aufarbeitung

  1. customTo a round bottomed flask equipped with a magnetic stir bar
  2. customthe solvent was completely evaporated
  3. filtrationYellow solid was filtered
  4. washwashed with DCM

Quellen und Nachweise

ORD-Eintrag
ord-84f5c49191eb40e98ac319cd334e1ac0
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691187B2

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