4-Chloro-1,2-diaminobenzene → HCID 178526559, Verbindung

HRID 1263536

Reaktionsgleichung

Reaktionsgleichung von HRID 1263536
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[N+:10]([C:13]1[C:14]([NH2:20])=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].Cl.Cl.[C:23](=N)(OCC)[CH2:24][C:25](=N)OCC>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:23]([CH2:24][C:25]3[NH:19][C:15]4[CH:16]=[CH:17][CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[C:14]=4[N:20]=3)=[N:9][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 72634-Chloro-1,2-diaminobenzeneHCID 73106Diethyl malonimidateHCID 43595253-Nitro-1,2-phenylenediamine

Produkt 1

HCID 178526559HCID 178526559, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a flame-dried 100 mL round-bottom flask equipped with a stir bar and a reflux condenser were added 4-chloro-1,2-phenylenediamine (1 g; 7.0 mmoles), 3-nitro-1,2-phenylenediamine (1.07 g; 7.0 mmoles), diethyl malonimidate dihydrochloride (1.62 g; 7.0 mmoles) and ultra pure acetic acid (ca. 35 mL; from Aldrich) under a nitrogen atmosphere. The mixture was refluxed for 2 hours and then cooled to room temperature, and the acetic acid was removed (via roto-vap). The residue was suspended and sonicated (ca. 5 minutes) in 0.5 M HCl, and the remaining precipitate was removed by filtration and dried (P2O5 and high-vacuum). This procedure gave 0.8 g of the desired 2-[(5-chloro-1H-benzimidazol-2-yl)methyl]4-nitro-1H-benzimidazole as a dark brown solid in 35% yield. It gave one major peak by HPLC and had mass spec (FB+): m/z=328.0 [M+].

Aufarbeitung

  1. customTo a flame-dried 100 mL round-bottom flask equipped with a stir bar and a reflux condenser
  2. temperatureThe mixture was refluxed for 2 hours
  3. customthe acetic acid was removed (via roto-vap)
  4. customsonicated (ca. 5 minutes) in 0.5 M HCl
  5. customthe remaining precipitate was removed by filtration
  6. dry with materialdried (P2O5 and high-vacuum)

Quellen und Nachweise

ORD-Eintrag
ord-f129fa78cdd24784a584d86f7efeade8
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541486B1

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