تفاعل #1605770

معادلة التفاعل

2,4-dimethoxybenzylamine

triethylamine

Ethyl chlorooxoacetate

→

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

المردود 92.8%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىA clean and dry jacketed reactor
2. 2
   أخرىwas equipped with a condenser
3. 3
   أخرىThe 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
   أخرىdid not exceed 10° C
6. 6
   أخرىSolids formed approximately ⅓ into the addition
7. 7
   workup.ADDITIONAfter the addition
8. 8
   درجة الحرارةWhen complete, the reaction was warmed to from 20° C. to 25° C
9. 9
   غسيلThe organic phase was washed twice with 22,580 mL of 1 N HCl
10. 10
    غسيلThe organic phase was then washed with 12,600 mL saturated sodium bicarbonate
11. 11
    غسيلNext, the organic phase was washed with 12,463 mL of brine
12. 12
    تجفيفdried over magnesium sulfate
13. 13
    ترشيحThe mixture was filtered through a thin pad of celite
14. 14
    تركيزconcentrated at from 40° C. to 45° C. to a yellow oil

الإجراء التجريبي

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.

المصدر