반응 #2139930

반응 방정식

N,N-diphenylhydrazine hydrochloride

4-diethylamino-2-hydroxybenzaldehyde

sodium carbonate

→

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

용매

ethanol

ethanol

반응 조건

후처리

1. 1
   기타reacted in about ½ hour
2. 2
   기타The residue obtained
3. 3
   기타after evaporation of the solvent (800 ml)
4. 4
   workup.ADDITIONwas treated with ether
5. 5
   추출the ether extract
6. 6
   세척was washed with water until the pH of the water
7. 7
   건조The organic layer was dried over anhydrous magnesium sulphate
8. 8
   workup.ADDITIONtreated with activated charcoal
9. 9
   여과filtered
10. 10
    기타The ether solvent was evaporated
11. 11
    기타the residue was recrystallized from ethanol
12. 12
    여과Crystalline 4-diethylamino-2-hydroxybenzaldehyde N,N-diphenylhydrazone was filtered off
13. 13
    세척washed with cold ethanol
14. 14
    기타to be 95.5-96.5° C.
15. 15
    기타recrystallized from a mixture of 2-propanol and ether in a 10:1 ratio by volume)
16. 16
    기타An elemental analysis yielded the
17. 17
    기타following results in weight percent

실험 절차

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. The ether solvent was evaporated and the residue was recrystallized from ethanol. Crystalline 4-diethylamino-2-hydroxybenzaldehyde N,N-diphenylhydrazone was filtered off and washed with cold ethanol. The yield of the product 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.

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