N-Methylethylamine → 2-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]nitrobenzene

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Reaction Steps

2-Chloro-3-fluoro-4-(4-carboxyphenylsulphanyl)nitrobenzene (Method 24; 5.5 g, 16.8 mmol) was suspended with stirring in DCM (100 ml) and oxalyl chloride (3.22 ml) was added. A couple of drops of DMF were added to initiate the reaction and it was left to stir overnight. The mixture was evaporated to dryness and then redissolved in DCM (20 ml). N-ethyl-N-methylamine (0.46 ml, 5.28 mmol) was dissolved in DCM (1 ml) and to this with stirring was added some of the above acid chloride solution (2.4 mmol). The solution was left to stir overnight and then washed with water, brine and dried by pouring onto a Chem Elut column eluting with EtOAc. The resulting solution was evaporated down to dryness and then purified by chromatography on a Mega Bond Elut column eluting with a graduated solvent of hexane/EtOAc to yield the title compound (680 mg). NMR: 1.1 (s, 3H), 2.9 (d, 3H), 3.2 (s, 1H), 3.4 (s, 1H), 7.2 (m, 1H), 7.5 (d, 2H), 7.6 (d, 2H), 8.0 (m, 1H); m/z 369.

Provenance & Evidence