反应 #355756

反应方程式

N,N-diphenylhydrazine hydrochloride

4-diethylamino-2-hydroxybenzaldehyde

sodium carbonate

→

4-Diethylamino-2-hydroxybenzaldehyde N,N-diphenylhydrazone

溶剂

ethanol

ethanol

反应条件

后处理

1. 1
   其他reacted in about ½ hour
2. 2
   其他The residue obtained
3. 3
   其他after evaporation of the solvent (800 ml)
4. 4
   workup.ADDITIONwas treated with ether
5. 5
   萃取the ether extract
6. 6
   洗涤was washed with water until the pH of the water
7. 7
   干燥The organic layer was dried over anhydrous magnesium sulphate
8. 8
   workup.ADDITIONtreated with activated charcoal
9. 9
   过滤filtered
10. 10
    其他Next, the ether solvent was evaporated
11. 11
    其他The residue was recrystallized from ethanol
12. 12
    过滤Crystalline 4-diethylamino-2-hydroxybenzaldehyde N,N-diphenylhydrazone was filtered off
13. 13
    洗涤washed with cold ethanol
14. 14
    其他to be 95.5-96.5° C.
15. 15
    其他recrystallized from a mixture of 2-propanol and ether in a 10:1 ratio by volume)
16. 16
    其他An elemental analysis yielded the
17. 17
    其他following results in weight percent

实验过程

A solution of N,N-diphenylhydrazine hydrochloride (79.5 g, 0.36 mol, from Aldrich, Milwaukee, Wis.) in ethanol (500 ml) was slowly added to a solution of 4-diethylamino-2-hydroxybenzaldehyde (58.0 g, 0.3 mol, from Aldrich, Milwaukee, Wis.) in ethanol (500 ml) in the presence of excess sodium carbonate. The reaction mixture was refluxed until all of the aldehyde reacted in about ½ hour. The residue obtained after evaporation of the solvent (800 ml) was treated with ether and the ether extract was washed with water until the pH of the water reached 7. The organic layer was dried over anhydrous magnesium sulphate, treated with activated charcoal, and filtered. Next, the ether solvent was evaporated. The residue was recrystallized from ethanol. Crystalline 4-diethylamino-2-hydroxybenzaldehyde N,N-diphenylhydrazone was filtered off and washed with cold ethanol. The yield was 85 g (78.8%). The melting point was found to be 95.5-96.5° C. (recrystallized from a mixture of 2-propanol and ether in a 10:1 ratio by volume). The 1H-NMR spectrum (100 MHz) of the product in CDCl3 was characterized by the following chemical shifts (δ, ppm): 11.55 (s, 1H, OH); 7.55-6.95 (m, 11H, CH═N, Ph); 6.7 (d, J=8.6 Hz; 1H, 6-H of 1,2,4-subst. Ph); 6.23 (s, 1H, 3-H of 1,2,4-subst. Ph); 6.1 (d, J=8.6 Hz, 1H, 5-H of 1,2,4-subst. Ph); 3.3 (q, J=8.0 Hz, 4H, CH2); 1.1 (t, J=8.0 Hz, 6H, CH3). An elemental analysis yielded the following results in weight percent: C, 76.68; H, 7.75; N, 11.45, which compared with calculated values for C23H25N3O in weight percent of: C, 76.85; H, 7.01; N, 11.69.

来源