Potassium Hydroxide → 4-[[(2,2-Dichloro-1-methylcyclopropyl)methyl]thio]-2-nitrobenzenamine

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Reaction Steps

To a stirred mixture 9.75 g (0.05 mole) of 2-nitro-4-thiocyanoaniline in 500 ml of absolute ethanol under N2, there is added 2.1 g of sodium borohydride in portions. The mixture is stirred at room temperature for 3 hours. 3.25 g (0.05 mole) of KOH in 30 ml of absolute ethanol is added. The mixture is stirred for 1 minute. A solution of 8.7 g (0.05 mole) of 1,1-dichloro-2-chloromethyl-2-methylcyclopropane in 15 ml of absolute ethanol is added and the mixture is refluxed for 3 hours. Equal amounts of H2O and CHCl3 are added until two layers are formed. The organic layer is separated, dried (MgSO4), and the solvent removed in vacuo to give a red oil which is triturated with 10 ml of absolute ethanol to yield 9.6 g of 2-nitro-4-[(2,2-dichloro-1-methylcyclopropyl)methyl]thioaniline as a solid, m.p. 76-78° C.

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