反応 #56117

反応方程式

Mesyl chloride

methylene chloride

1-(2',6'-dichlorophenyl)-2-(2',3'-bis-methoxycarbonylguanidino) ethanol

triethylamine

→

4,5-dihydro-2-methoxycarbonylamino-5-(2',6'-dichlorophenyl)imidazole

収率 92.6%

溶媒

methanol

反応条件

後処理

1. 1
   その他formed
2. 2
   workup.STIRRINGwith stirring at such a rate that the solution temperature
3. 3
   その他did not pass 35° C
4. 4
   ろ過the resulting mixture filtered
5. 5
   workup.ADDITIONTo the filtrate was added 4 l of methanol
6. 6
   workup.STIRRINGThe mixture was vigorously agitated
7. 7
   workup.DISTILLATIONvacuum distilled until approximately 5 l of distillate
8. 8
   その他had been collected
9. 9
   workup.ADDITIONAfter addition of 8 l of deionized water
10. 10
    workup.DISTILLATIONto the distillation flask, vacuum distillation
11. 11
    workup.DISTILLATIONcollecting 3 l of distillate
12. 12
    温度The pot residue was cooled to about 20° C.
13. 13
    workup.STIRRINGstirred for about 1 hour
14. 14
    その他The imidazole product precipitated from the residual reaction solution
15. 15
    ろ過was filtered
16. 16
    洗浄washed with 3 l of deionized water
17. 17
    その他Drying at 65° C. in a vacuum oven

実験手順

To 5 l of a methylene chloride solution containing 550 g of 1-(2',6'-dichlorophenyl)-2-(2',3'-bis-methoxycarbonylguanidino) ethanol was added 530 ml of triethylamine. The mixture was stirred until a clear solution formed. Mesyl chloride, 160 ml was then added dropwise with stirring at such a rate that the solution temperature did not pass 35° C. The reaction was complete after 30 minutes. One liter of methanol was added to the reaction mass and the resulting mixture filtered. To the filtrate was added 4 l of methanol and a solution of 270 g of sodium hydroxide in 550 ml of deionized water. The mixture was vigorously agitated and heated to about 40° C. for one hour. The reaction solution was then vacuum distilled until approximately 5 l of distillate had been collected. After addition of 8 l of deionized water to the distillation flask, vacuum distillation was continued, collecting 3 l of distillate. The pot residue was cooled to about 20° C. and stirred for about 1 hour. The imidazole product precipitated from the residual reaction solution and was filtered, washed with 3 l of deionized water then 1 liter of methanol. Drying at 65° C. in a vacuum oven gave 403 g of 4,5-dihydro-2-methoxycarbonylamino-5-(2',6'-dichlorophenyl)imidazole, m.p. 231°-232° C. (dec.).

出典