2,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene → HCID 86743153, compound

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Reaction Conditions

Reaction Steps

6.71 g (0.022 mole) of 1,3-dichloro-2,6-dinitro-4-trifluoromethylbenzene and 3.56 g (0.020 mole) of 5-amino-4,6-dichloro-2-methylpyrimidine are dissolved in 50 ml of tetrahydrofuran. The solution is cooled to -30° C. and, at this temperature, a solution of 4.6 g (0.041 mole) of potassium tert-butylate in 50 ml of tetrahydrofuran is added dropwise. After 1 hour at -30° to 0° C., the mixture is extracted with water and ethyl acetate while adding 10 ml of acetic acid. The extracts are dried over sodium sulfate and concentrated, affording 10.5 g of an oil as crude product. This product is purified by chromatography through a column of silica gel using a mixture of 3 parts of petroleum ether and 1 part of ethyl acetate. The solvent is removed by rotary evaporation, affording 8.3 g of product as residue. Recrystallisation from a mixture of toluene and cyclohexane yields 6.80 g (69.2% of theory) of yellow crystals with a melting point of 134°-136° C.

Provenance & Evidence