1: 1-((2'-cyanobiphenyl-4-yl)methyl)-4-methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid With thionyl chloride; N,N-dimethyl-formamide in dichloromethane T=0°C; Reflux; 2: N-methyl-1,2-phenylenediamine dihydrochloride With sodium carbonate; sodium chloride in water; ethyl acetate T=-20 - 5°C; 1 h; 3: With boric acid in toluene T=10 - 15°C; Reflux; Product distribution / selectivity;

1: With PPA T=70 - 135°C; 13.5 h; 2: With ammonia in water T=30 - 90°C; pH=8.0 - 8.5; 1 h;

1: 5.86 g / polyphosphoric acid / 20 h / 150 °C 2: 1.) t-BuOK / 1.) DMSO, RT, 30 min, 2.) DMSO, 14 h 3: CF3COOH / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 61 percent / 2 N aq. HCl / 18 h / Heating 2: 87 percent / ethanol / 0.75 h / 0 °C View Scheme

phosphoric acid T=200°C; 4 h;

ethanol; water; copper diacetate

in hydrogenchloride

ethanol; copper diacetate Behandeln des Reaktionsprodukts in wss. HCl mit H2S;

ethanol; copper diacetate Behandeln des Reaktionsprodukts in siedendem wss. HCl mit H2S;