Hydrochloric Acid → Triazamate

Participants

Reaction Steps

To a solution of 813 g (3.34 mole) of 3-t-butyl-5-carboethoxymethylthio-1,2,4-1H-triazole in 2 liters of THF was added 395 g (3.67 mole) of dimethyl carbamoyl chloride and 50 g (0.4 mole) of 4-dimethylaminopyridine. To this solution is slowly added 675 g (6.68 mole) of triethylamine, whereon the reaction exotherms to reflux. The reaction is allowed to react for an additional 1.5 hours whereon the temperature slowly returns to room temperature. One liter of ethyl ether, 2 liters of water, 2 kgs of ice are added and the mixture is acidified with concentrated aqueous hydrochloric acid. The aqueous layer is separated and backwashed with 1 liter of ethyl ether before discarding. The combined aqueous layers are washed with 2 liters of brine, dried over magnesium sulfate, and concentrated under vacuum to afford 1016 g of 1-dimethylcarbamoyl-3-t-butyl-5-carboethoxymethylthio-1,2,4-1H-triazole as a tan solid.

Provenance & Evidence