Oxalic Acid → 2-(3-Bromophenyl)benzimidazole

HRID 2047399

Reaktionsgleichung

Reaktionsgleichung von HRID 2047399
[2H][C:2]1[C:7]([2H])=[C:6]([NH2:9])[C:5]([NH2:10])=[C:4]([2H])[C:3]=1[2H].C(O)(=O)C(O)=O.[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O>C(O)C.O>[Br:19][C:20]1[CH:21]=[C:22]([C:23]2[NH:10][C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][C:6]=3[N:9]=2)[CH:25]=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 971Oxalic AcidHCID 765833-BromobenzaldehydeHCID 107729501,2-Diaminobenzene (D4, 98%)

Produkt 1

HCID 2788222-(3-Bromophenyl)benzimidazoleAusbeute 26,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

O-phenylenediamine (81.8 g, 756.6 mmol) and oxalic acid (3.4 g, 37.8 mmol) were completely dissolved in EtOH—H2O/1:1 (2 L) previously warmed at 80° C. 3-Bromobenzaldehyde (44.10 mL, 378.30 mmol) was then added dropwise to the solution. The reaction mixture was stirred overnight at 70° C. to the open air. The day after solid was filtered off and triturated with MeOH (150 mL) to give the product as a pale yellow solid (27.50 g). 3.8 g were recovered from the mother liquors. Total yield 31.30 g (30%).

Aufarbeitung

  1. filtrationThe day after solid was filtered off
  2. customtriturated with MeOH (150 mL)

Quellen und Nachweise

ORD-Eintrag
ord-22885e3db09647e7ade31aa8bd08e47d
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592463B2

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