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1-(2-Hydroxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-thione[ No CAS ]
[ 153587-01-0 ]
Yield
Reaction Conditions
Operation in experiment
In dichloromethane;
EXAMPLE 6 1-(2-Hydroxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-one. A suspension of 1-(2-Methoxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-one (70 mmol, 26.3 g) in absolute methylenechloride is added borontribromide (84 mmol, 7.94 ml). After stirring at room temperature for four hours the reaction mixture is poured into water and the title compoundcompound is collected by filtration as white crystals, M.p. 228-231C. The following compound is prepared in a similar manner. 1-(2-Hydroxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-thione, M.p. decompose at 160C.
In dichloromethane;
EXAMPLE 6 1-(2-Hydroxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-one. A suspension of 1-(2-Methoxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-one (70 mmol, 26.3 g) in absolute methylenechloride is added borontribromide (84 mmol, 7.94 ml). After stirring at room temperature for four hours the reaction mixture is poured into water and the title compoundcompound is collected by filtration as white crystals, M.p. 228-231 C. The following compound is prepared in a similar manner. 1-(2-Hydroxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-thione, M.p. decompose at 160 C.
5-trifluoromethyl-2,3-dihydro-1-(3-nitro-5-trifluoromethyl-2-hydroxyphenyl)-1H-2-oxo-benzimidazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium nitrate; In sulfuric acid;
EXAMPLE 7 1-(2-Hydroxy-3-nitro-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-one. To an ice cooled solution of 1-(2-Hydroxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-one (1.38 mmol, 0.50 g) in concentrated sulphuric acid (6 ml) is added an ice cooled solution of potassium nitrate (1.38 mmol, 0.14 g) in concentrated sulphuric acid (8 ml). The reaction mixture is allowed to reach room temperature and is poured into ice. The crude product is collected by filtration and subjected to column chromatography using methylenechloride+methanol (9+1) as eluent. The fractions containing the product are concentrated in vacuo yielding the title compound as slightly yellow crystals, M.p.>360 C.
5-trifluoromethyl-2,3-dihydro-1-(3-nitro-5-trifluoromethyl-2-hydroxyphenyl)-1H-2-oxo-benzimidazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium nitrate; In methanol; sulfuric acid;
EXAMPLE 7 1-(2-Hydroxy-3-nitro-5-trifluoromethylphenyl)-5-trifluoromethyl- 1,3-dihydro-2H-benzimidazol-2-one. To an ice cooled solution of 1-(2-Hydroxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-one (1.38 mmol, 0.50 g) in concentrated sulphuric acid (6 ml) is added an ice cooled solution of potassium nitrate (1.38 mmol, 0.14 g) in concentrated sulphuric acid (8 ml). The reaction mixture is allowed to reach room temperature and is poured into ice. The crude product is collected by filtration and subjected to column chromatography using methylenechloride + methanol (9+1) as eluent. The fractions containing the product are concentrated in vacuo yielding the title compound as slightly yellow crystals, M.p. >360C.
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