Triethylamine → N-(3-methylpent-1-yn-3-yl)-4-nitrobenzamide

Participants

Reaction Steps

In a three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 4 grams (g) (0.03 mole) of 3-amino-3-methyl-1-pentyne hydrochloride (4 grams (g) (0.03 mole) suspended in 100 milliliters (mL) of methylene chloride in a three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer. Triethylamine (6.82 g, 9.4 mL) was added slowly, keeping the temperature between 5° C. and 10° C. 4-nitrobenzoyl chloride 5 g (0.027 mole) was added to the resulting mixture at a rate to keep the reaction temperature between 5° C. and 10° C. After the addition was complete the reaction mixture was stirred at room temperature for 0.5 hours, and was then sequentially washed with water (2×100 mL), 5% aqueous hydrochloric acid, (2×100 mL), water (1×50 mL), 5% aqueous sodium hydroxide (2×100 mL) and finally with water (1×100 mL) before being dried over anhydrous magnesium sulfate. The solvent was removed in the rotary evaporator, yielding N-(3-methylpent-1-yn-3-yl)-4-nitrobenzamide, used as such in the next step.

Provenance & Evidence