EXPERIMENTAL PRODEDURE:

STEP 1: Synthesis of N-phenyl-1,2-benzenediamine

To a solution of compound 4 (2.9g, 10 mmol) in DMSO (50 ml) was

added freshly distilled aniline 5 (4.6ml, 50 mmol). The reaction was
heated to 70 ⁰C and stirred for 8h. The reaction was cooled to 22 C
and poured into water (200 ml). The aqueous phase was extracted
with diethyl ether (100 ml, 4). The organic extracts were combined
and washed with saturated aqueous NaCl (200 ml), dried over
anhydrous Na2SO4 and concentrated in vacuo. The residue was
purified by column chromatography (CH2Cl2 eluent) to afford the
product (2.46g, 71%) as an orange solid. (6)

Mp: 160-162 Oc

TLC hexane/ethyl acetate, 3:1

STEP 2: To a slurry of compound 6 (1.74g, 5mmol) in ethanol (50 ml)

was added palladium on carbon 10% (530mg, 0.5mmol) and
anhydrous hydrazine (0.5ml , 16mmol). The reaction was heated to
80 oC and refluxed for 30 min. the reaction was cooled to 22oC and
filtered through a fritted funnel. The solid Pd/C was washed with
ethanol (10 ml) and the combined filtrate was concentrated in vacuo
to afford the crude product. Recrystallization from CH2Cl2/hexane
afforded the product (1.52g, 95%) as a light- yellow solid.

Mp: 154-156

Ref: http://pubs.acs.org/doi/ipdf/10.1021/jm100912b

STEP 3: Synthesis of 1,2-diphenyl-1H-benzimidazole

Synthesis of benzimidazoles via metal-free aerobic oxidation in wet DMF
(Table 5)
General procedure: An ortho-phenylenediamine derivative 3 (1.0 mmol; 1.0 equiv)
and an aldehyde 4 (1.0 mmol; 1.0 equiv) were dissolved in wet DMF (DMF 9.0 mL,
H2O 1.0 mL). The resulting reaction mixture was stirred at 80°C in an open flask,
and the reaction progress was monitored by TLC. On the complete consumption of
3, the reaction mixture was cooled to room temperature and concentrated under
reduced pressure. The crude product obtained was purified by column
chromatography on silica gel to afford the corresponding benzimidazole 5

OR STEP 3:

STEP 3: The pure N-phenyl-o-phenylenediamine (3.128 g, 17 mmol) in ethanol (10 ml),

benzaldehyde (1.72 ml, 17 mmol) and ammonium acetate (3 g) was added about 1 h by
maintaining the temperature at 353 K. The reaction mixture was refluxed for appropriate
time and the completion of reaction was monitored by TLC, finally the reaction extracted
with dichloromethane. The solid separated was purified by column chromatography using
petroleum ether: ethyl acetate as the eluent. Yield: 2.49 g (50%). The title compound was
dissolved in acetonitrile and allowed to slow evaporation for two days to obtain crystals
suitable for X-ray diffraction studies.

https://www.researchgate.net/publication/235882853_12-Diphenyl-1H-benzimidazole

COSTING:
References:

1. Synthesis and Biological Evaluation of Analogues of AKT (Protein

Kinase B) Inhibitor-IV

Qi Sun†, Runzhi Wu†, Sutang Cai†, Yuan Lin§, Llewlyn Sellers‡, Kaori Sakamoto‡, Biao He§, and Blake R. Peterson*†

†
Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66047, United States

‡
Departments of Pathology and §Infectious Diseases, The University of Georgia College of Veterinary Medicine, Athens,

Georgia 30602, United States

J. Med. Chem., 2011, 54 (5), pp 1126–1139 DOI: 10.1021/jm100912b

Publication Date (Web): February 14, 2011