反应详情

To a solution of 500 g (4.2 moles) of 4-vinylaniline and 460 g (4.2 moles) of triethylamine in 1000 cc of anhydrous diethyl ether under a nitrogen atmosphere was added dropwise 478 g (4.2 moles) of methanesulfonyl chloride. The temperature of the reaction vessel was kept below 5° C. by an ice bath during the course of the reaction. When addition was complete (40 min.), the mixture was stirred for an additional 2 hours and the contents of the flask then brought to room temperature. The mixture was filtered and extracted with 500 cc of 1.0 M HCl solution. The etheral portion was separated, dried and the ether removed on a rotary evaporator. The resulting oily solid was extracted with 500 cc of ethanol and recrystallized from ethane/water and then from toluene. 70-75% yield after recrystallization. M.P. = 97° C.

1. customThe temperature of the reaction vessel was kept below 5° C. by an ice bath during the course of the reaction
2. additionWhen addition
3. custom(40 min.)
4. customthen brought to room temperature
5. filtrationThe mixture was filtered
6. extractionextracted with 500 cc of 1.0 M HCl solution
7. customThe etheral portion was separated
8. customdried
9. customthe ether removed on a rotary evaporator
10. extractionThe resulting oily solid was extracted with 500 cc of ethanol
11. customrecrystallized from ethane/water
12. custom70-75% yield after recrystallization