Sodium Carbonate → 3-(Diethylamino)-6-[(2,2-diphenylhydrazinyl)methylidene]-1-cyclohexa-2,4-dienone

HRID 32281

반응식

HRID 32281 반응식
Cl.[C:2]1([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([N:18]([CH2:28][CH3:29])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[C:21]([OH:27])[CH:20]=1)[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:2]1([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:9]=[CH:23][C:22]2[CH:25]=[CH:26][C:19]([N:18]([CH2:28][CH3:29])[CH2:16][CH3:17])=[CH:20][C:21]=2[OH:27])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)HCID 872934-(Diethylamino)-2-hydroxybenzaldehyde2회

생성물 1

HCID 33912063-(Diethylamino)-6-[(2,2-diphenylhydrazinyl)methylidene]-1-cyclohexa-2,4-dienone

시약·촉매·용매 1

HCID 702Ethanol용매2회

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 4-diethylamino-2-hydroxybenzaldehyde was completely reacted in about 30 minutes. The solvent (800 ml) was removed by evaporation. The residue obtained was extracted with diethyl 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 sulfate, treated with activated charcoal, and filtered. The ether solvent was evaporated. The residue was recrystallized from ethanol to form crystals. The crystals were filtered off and washed with cold ethanol. The product was 4-diethylamino-2-hydroxybenzaldehyde N,N-diphenylhydrazone. The yield of the product was 85 g (78.8%). The melting point of the product 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.

후처리

  1. customwas completely reacted in about 30 minutes
  2. customThe solvent (800 ml) was removed by evaporation
  3. customThe residue obtained
  4. extractionwas extracted with diethyl ether
  5. extractionthe ether extract
  6. washwas washed with water until the pH of the water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. additiontreated with activated charcoal
  9. filtrationfiltered
  10. customThe ether solvent was evaporated
  11. customThe residue was recrystallized from ethanol
  12. customto form crystals
  13. filtrationThe crystals were filtered off
  14. washwashed with cold ethanol
  15. customto be 95.5-96.5° C.
  16. customrecrystallized from a mixture of 2-propanol and ether in a 10:1 ratio by volume)
  17. customAn elemental analysis yielded the
  18. customfollowing results in weight percent

출처 및 근거

ORD 기록
ord-ad26332308f349028a8a6e3af79f8bd5
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427460B2

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