반응 #1605770

반응 방정식

2,4-dimethoxybenzylamine

triethylamine

Ethyl chlorooxoacetate

→

N-(2,4-dimethoxy-benzyl)-oxalamic acid ethyl ester

수율 92.8%

용매

THF

반응 조건

후처리

1. 1
   기타A clean and dry jacketed reactor
2. 2
   기타was equipped with a condenser
3. 3
   기타The reactor was flushed with nitrogen gas for at least 15 minutes
4. 4
   workup.ADDITIONhead column and charged to the batch at such a rate that the internal temperature
5. 5
   기타did not exceed 10° C
6. 6
   기타Solids formed approximately ⅓ into the addition
7. 7
   workup.ADDITIONAfter the addition
8. 8
   온도When complete, the reaction was warmed to from 20° C. to 25° C
9. 9
   세척The organic phase was washed twice with 22,580 mL of 1 N HCl
10. 10
    세척The organic phase was then washed with 12,600 mL saturated sodium bicarbonate
11. 11
    세척Next, the organic phase was washed with 12,463 mL of brine
12. 12
    건조dried over magnesium sulfate
13. 13
    여과The mixture was filtered through a thin pad of celite
14. 14
    농축concentrated at from 40° C. to 45° C. to a yellow oil

실험 절차

A clean and dry jacketed reactor was equipped with a condenser, a Claisen adapter, a temperature probe, and an addition funnel or head column. The reactor was flushed with nitrogen gas for at least 15 minutes. The reactor was then charged with 1,396 g (1 equiv., 8.3 mol) of 2,4-dimethoxybenzylamine, 1,693 g (2 equiv., 16.7 mol) of triethylamine, and 25,086 mL of THF. The mixture was cooled to from 0 to 5° C. Ethyl chlorooxoacetate (1140 g, 1 equiv., 8.3 mol) was added to an addition funnel or head column and charged to the batch at such a rate that the internal temperature did not exceed 10° C. Solids formed approximately ⅓ into the addition. After the addition was complete, the cooling was turned off and the slurry was allowed to stir for 30 minutes at from 5° C. to 15° C. When complete, the reaction was warmed to from 20° C. to 25° C. The organic phase was washed twice with 22,580 mL of 1 N HCl. The organic phase was then washed with 12,600 mL saturated sodium bicarbonate. Next, the organic phase was washed with 12,463 mL of brine and dried over magnesium sulfate. The mixture was filtered through a thin pad of celite and concentrated at from 40° C. to 45° C. to a yellow oil. A total of 2,052 g (7.7 mol, 92%) of the crude N-(2,4-dimethoxy-benzyl)-oxalamic acid ethyl ester was isolated.

출처