Dimethyl Sulfoxide → 2-Methoxy-6-[(methylsulfanyl)methyl]aniline

Participants

Reaction Steps

To a solution of 1.429 g (0.018 moles) of dry dimethyl sulfoxide and 2.27 g (0.015 moles) of dry n-butanesulfonic acid in 13 ml of dry chloroform, was added 2.2110 g (0.0148 moles) of o-methoxyphenyl isocyanate. After thirty minutes at room temperature, the reaction mixture was refluxed for three and a half hours. After cooling to room temperature, the reaction mixture was poured into 180 ml of ice-cold 10% aqueous sodium hydroxide solution. After extracting with methylene chloride, the organic layer was dried over anhydrous sodium carbonate, filtered and 0.10 g of succinimide was added. The resulting solution was concentrated to 100 ml and then refluxed for twenty hours. This solution was cooled, extracted with 10% aqueous sodium hydroxide solution and the organic layer dried over anhydrous magnesium sulfate and filtered. At this point, tridecane was added as an internal standard and the solution was analyzed by gas chromatography. In this manner, there was obtained 0.338 g (22.4%) of o-methoxyaniline and 1.8319 g (67.6%) of 2 -methoxy-6-(methylthiomethyl)aniline. The results are included in Table II.

Provenance & Evidence