1,1'-Carbonyldiimidazole → 5-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-one

HRID 2401488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401488
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([NH2:11])=[C:4]([NH2:12])[CH:3]=1.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C1COCC1>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]2[NH:11][C:18](=[O:19])[NH:12][C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57026184-Chloro-5-nitro-o-phenylenediamine

Produkt 1

HCID 145662265-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-oneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 4-chloro-5-nitro-1,2-phenylenediamine (2.0 g, 10.66 mmol) and CDI (2.59 g, 16 mmol) in anhydrous THF (50 mL) was heated to 85° C. for 4 h. The reaction was allowed to cool and the solvents were removed under reduced pressure. The resulting residue was washed with 2M aqueous hydrochloric acid and recrystallised from methanol to afford 5-chloro-6-nitro-1H-benzo[d]imidazol-2(3H)-one as a brown solid (1.9 g, 84%), which was taken through to the next step with no further purification.

Aufarbeitung

  1. temperatureto cool
  2. customthe solvents were removed under reduced pressure
  3. washThe resulting residue was washed with 2M aqueous hydrochloric acid
  4. customrecrystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-e68b6d7080e049eaa3e7dcf43a4664da
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796296B2

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