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With iron; ammonium chloride; In ethanol; water; at 60℃; for 0.5h;
A mixture of crude 2-amino-3- nitrobenzonitrile (150.0 mg, 920 imol, 1.0 eq), Fe (257 mg, 4.6 mmol, 5.0 eq), NH4C1 (246 mg, 4.6 mmol, 5.0 eq) in EtOH (3 mL) and water (1.5 mL) was stirred at 60C for 0.5 hour. The mixture was filtered and the filtrate was evaporated under reduced pressure to give aresidue. It was diluted with 5 mL of water and 5 mL of EtOAc, the organic layer was separated and washed once with 2 mL of brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give 50.0 mg of crude 2,3-diaminobenzonitrile as a brown solid which was used in the next step without further purification.
2,3-Diaminobenzonitrile (80 mg; may be prepared as described in intermediate 164) was taken up in ethanol (10 ml). Ethyl 3-bromo-2-oxopropanoate (0.076 ml; Aldrich) was added and left to stir at room temperature overnight. The reaction mixture was filtered, leaving a light orange solid as the residue (15mg). The filtrate was concentrated under vacuum. It was then diluted with DCM and purified, along with the residue, using silica chromatography (10 - 70% EtOAc / isohexane) to give the title compound (70 mg) as an orange solid, m/z [M+H]+: 264.0 / 266.0. Retention time 0.72 min (LC/MS method 3).
To a 0C solution of <strong>[73629-43-3]2,3-<strong>[73629-43-3]diaminobenzonitrile</strong></strong> 1 (0.532 g, 4.0 mmol) in acetic acid (10 mL) was added tetramethylorthocarbonate (0.544 g, 4.0 mmol). The mixture was stirred at the room temperature for 12 hours and then concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, petroleum ether / ethyl acetate= 10: 1) to give 2- methoxy-lH-benzo[d]imidazole-4-carbonitrile 2 (0.61 g, 88%). LRMS (M + H+) m/z: calcd 174.06; found 174.17.
2-(trichloromethyl)-1H-benzo[d]imidazole-4-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With trifluoroacetic acid; In dichloromethane; at 18℃; for 2.0h;Inert atmosphere;
To a mixture of 2,3-diaminobenzonitrile (50.0 mg, 376 imol, 1.0 eq) in DCM (1 mL) was added <strong>[2533-69-9]methyl 2,2,2-trichloroethanimidate</strong> (86.1 mg, 488 imol, 1.3 eq), followed by the addition of TFA (107.0 mg, 939 imol, 2.5 eq). The mixture was stirred at 18C for 2 hours under N2 atmosphere. The mixture was diluted with 5 mL of DCM and filtered. The filtrate wasused directly into the next step without further purification. The 97.8 mg of cmde 2- (trichloromethyl)-1H-benzo[djimidazole-4-carbonitrile in 5 mL of DCM was obtained as a brown solution and used in the next step directly.
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