Acetylacetone → 6-Bromo-2-methyl-4-nitro-1H-benzo[d]imidazole

HRID 44464

Reaktionsgleichung

Reaktionsgleichung von HRID 44464
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][C:14](=O)CC(=O)C>CCO.Cl>[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]2[N:9]=[C:13]([CH3:14])[NH:8][C:6]=2[CH:7]=1

Komponenten

5

Edukt 2

HCID 31261AcetylacetoneHCID 457894035-Bromo-3-nitrobenzene-1,2-diamine

Produkt 1

HCID 669767706-Bromo-2-methyl-4-nitro-1H-benzo[d]imidazoleAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-3-nitrobenzene-1,2-diamine (464 mg) and pentane-2,4-dione (400 mg) in EtOH (27 mL) and 5 N HCl (7.4 mL) was refluxed for 3 h. The mixture was cooled to room temperature and the solvent was removed in-vacuo. The residue was dissolved in EtOAc and washed with aqueous NaHCO3 solution and brine. The organic layer was concentrated to afford the desired product as a solid (460 mg, 90%). 1H NMR (300 MHz, CDCl3) δ ppm 2.73 (s, 3H), 8.11 (d, 1H, J=1.8 Hz), 8.24 (d, 1H, J=1.8 Hz), 10.20 (s, 1H, s); LC-MS: m/e=256 [M+1]+

Aufarbeitung

  1. temperaturewas refluxed for 3 h
  2. customthe solvent was removed in-vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with aqueous NaHCO3 solution and brine
  5. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-8db289205d6e4a8c89958eb31095a8e8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541411B2

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