Ammonium Chloride → 2-(5-Chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile

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Reaction Steps

Dissolve 2-amino-5-methyl-thiophene-3-carbonitrile (0.79 g, 5.7 mmol) and 2-fluoro-4-chloronitrobenzene (1 g, 5.7 mmol) in dimethylsulfoxide (15 ml) and stir under nitrogen. Add lithium hydroxide monohydrate (250 mg, 6 mmol) and heat the mixture in an oil bath at 60° C. overnight. Pour the mixture into sat. NH4Cl(aq), extract into ethyl acetate, dry (MgSO4) and concentrate under reduced pressure. Chromatography on silica gel (eluent cyclohexane/ethylacetate) gives 2-(5-chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile as a yellow solid (0.58 g, 35%): NMR (1H, 300 MHz, CDCl3): δ 9.6 (1H broad), 8.21 (1H,d), 7.09 (1H, s), 6.92 (1H,d), 6.80 (1H, s), 2.49 (3H,s).

Provenance & Evidence