Triethylamine → 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(tert-butylthiosulfenyl)-N-methylcarbamate

Participants

Reaction Conditions

Reaction Steps

In a manner identical to that described in Example II, Part A, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenol was prepared. To a 500 milliliter round bottom flask equipped with a water condenser, magnetic stirrer and drying tube was added 4.83 grams (0.020 moles) of 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenol, 3.95 grams (0.020 moles) of N-(tertbutylthiosulfenyl)-N-fluorocarbonyl-N-methylamine, 2.12 grams (0.021 moles) of triethylamine and 200 milliliters of toluene. The resulting reaction mixture was heated to a temperature of 50° C. in an oil batch for 16 hours with continuous stirring. After this heating and stirring period, 1.0 grams (0.0041 moles) of N-tert-butylthiosulfenyl)-N-fluorocarbonyl-N-methylamine and 0.5 grams (0.005 moles) of triethylamine were added to the reaction mixture and heating continued for an additional 3 hours at a temperature of 50° C. with continuous stirring. The reaction mixture was cooled to room temperature and then washed twice with water, twice with a 2% aqueous sodium bicarbonate solution and once with a saturated brine solution. After drying the reaction mixture over magnesium sulfate, it was concentrated under reduced pressure to give a red oil. Purification of the red oil by column chromatography yielded 2.02 grams (0.0048 moles) of 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(tert-butylthiosulfenyl)-N-methylcarbamate in the form of a yellow solid having a melting point of 121°-124° C. and the following structural formula: ##STR24##

Provenance & Evidence