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

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

In a 1000 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 10 g of 4-acetamido-3-nitrobenzoic acid, 200 mL of tetrahydrofuran and 31 mL of triethylamine. The resulting well-stirred mixture was cooled to -30° C. and 3.9 mL of methane sulfonyl chloride were added dropwise while keeping the reaction temperature at -30° C. The resulting suspension was stirred at -30° C. for 30 minutes, after which 6.7 g of 3-amino-3-methyl-1-pentyne hydrochloride were added slowly over a 20 minute period. After the addition was complete, the reaction mixture was stirred at -30° C. for an additional 30 minutes. The reaction mixture was then poured into a mixture of 400 mL water and 200 mL of ethyl acetate. The phases were separated and the aqueous layer was then extracted with ethyl acetate (2×150 mL). The combined organic phases were washed sequentially with water (1×200 mL), 5% aqueous hydrochloric acid (2×200 mL), water (1×200 mL), 2% aqueous sodium hydroxide (2×200 mL) and water (1×200 mL) and then dried over anhydrous magnesium sulfate. The solvent was removed in the rotary evaporator, yielding 8.2 g of N-(3-methylpent-1-yn-3-yl)-4-acetamido-3-nitrobenzamide.

Herkunft & Nachweise