反应 #1076774

反应方程式

methanol

2Methoxy-5-nitroaniline

methyl 2,2,5-trimethyl-b-oxo-1,3-dioxane-5-propanoate

m-xylene

→

N-(5-Nitro-2-methoxyphenyl)-2,2,5-trimethyl-b-oxo-1,3-dioxane-5-propanamide

溶剂

n-octane

反应条件

后处理

1. 1
   其他was continuously removed by a very slow nitrogen sweep
2. 2
   温度After 2 hr of heating the solution
3. 3
   温度to cool slowly with good stirring
4. 4
   其他the yellow-orange precipitate which formed
5. 5
   过滤was filtered
6. 6
   其他to air dry
7. 7
   workup.DISSOLUTIONThe crude precipitate was dissolved in ethyl ether
8. 8
   萃取extracted with dilute hydrochloric acid
9. 9
   洗涤after which the ethereal solution was washed once with dilute sodium bicarbonate, once with water
10. 10
    其他the organic and aqueous layers separated
11. 11
    干燥the organic layer dried over magnesium sulfate
12. 12
    过滤The mixture was filtered
13. 13
    其他the excess solvent removed in vacuo
14. 14
    其他The residue was recrystallized from ethyl alcohol, m.p. 113-5° C.

实验过程

2Methoxy-5-nitroaniline (63.06 g, 0.375 mol) and methyl 2,2,5-trimethyl-b-oxo-1,3-dioxane-5-propanoate (90.0 g, 0.391 mol) were dispersed in n-octane (500 mL) and m-xylene (100 mL) in a 2-liter three-necked flask. The mixture was heated at the boiling point while methanol was continuously removed by a very slow nitrogen sweep. After 2 hr of heating the solution was allowed to cool slowly with good stirring; the yellow-orange precipitate which formed was filtered and allowed to air dry. The crude precipitate was dissolved in ethyl ether and extracted with dilute hydrochloric acid, after which the ethereal solution was washed once with dilute sodium bicarbonate, once with water, the organic and aqueous layers separated, and the organic layer dried over magnesium sulfate. The mixture was filtered and the excess solvent removed in vacuo. The residue was recrystallized from ethyl alcohol, m.p. 113-5° C.; H-NMR was consistent. Elemental analysis calculated for C17H22N5O7: C, 55.73; H, 6.05; N, 7.65. Found: C, 55.64; H. 6.14; N, 7.53.

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