反应详情

温度

-30 °C

In a 100 ml, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 1.27 g (5.5 mmole) of the preceding 4-amino-3-chloro-5-methoxyiminomethylbenzoic acid, (25 ml of tetrahydrofuran and 2.31 ml (16.6 mmole) of triethylamine. The resulting well-stirred mixture was cooled to -30° C. and 0.47 ml (6.1 mmole) of methane sulfonyl chloride were added dropwise keeping the reaction temperature at -30° C. The resulting suspension was stirred at -30° C. during 30 minutes, after which 0.74 g (5.5 mmole) of 3-amino-3-methyl-1-pentyne hydrochloride were added over a 20 minute period. After the addition was completed, the reaction mixture was stirred at -30° C. for an additional 30 minutes. The reaction mixture was poured into water and extracted with methylene chloride (3×25 ml). The combined organic phases were washed sequentially with water (1×20 ml), 5% aqueous hydrochloric acid (2×20 ml), water (1×20 ml), 2% aqueous sodium hydroxide (2×20 ml) and then with water (1×20 ml) and dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, yielding 1.05 g of the expected N-(3-methylpent-1-yn-3-yl)-4-amino-3-chloro-5-methoxyiminomethylbenzamide, used in the next step without further purification.

1. customIn a 100 ml, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet
2. customat -30° C
3. stirringThe resulting suspension was stirred at -30° C. during 30 minutes
4. additionAfter the addition
5. stirringthe reaction mixture was stirred at -30° C. for an additional 30 minutes
6. extractionextracted with methylene chloride (3×25 ml)
7. washThe combined organic phases were washed sequentially with water (1×20 ml), 5% aqueous hydrochloric acid (2×20 ml), water (1×20 ml), 2% aqueous sodium hydroxide (2×20 ml)
8. dry with materialwith water (1×20 ml) and dried over anhydrous magnesium sulfate
9. customThe solvent was removed
10. customa rotary evaporator