反应 #1605770

反应方程式

2,4-dimethoxybenzylamine

triethylamine

Ethyl chlorooxoacetate

→

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

收率 92.8%

溶剂

THF

反应条件

后处理

1. 1
   其他A clean and dry jacketed reactor
2. 2
   其他was equipped with a condenser
3. 3
   其他The 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
   其他did not exceed 10° C
6. 6
   其他Solids formed approximately ⅓ into the addition
7. 7
   workup.ADDITIONAfter the addition
8. 8
   温度When complete, the reaction was warmed to from 20° C. to 25° C
9. 9
   洗涤The organic phase was washed twice with 22,580 mL of 1 N HCl
10. 10
    洗涤The organic phase was then washed with 12,600 mL saturated sodium bicarbonate
11. 11
    洗涤Next, the organic phase was washed with 12,463 mL of brine
12. 12
    干燥dried over magnesium sulfate
13. 13
    过滤The mixture was filtered through a thin pad of celite
14. 14
    浓缩concentrated at from 40° C. to 45° C. to a yellow oil

实验过程

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.

来源