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

HRID 349142

반응식

HRID 349142 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 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. Crystals were filtered off and washed with cold ethanol. The product was 4-diethylamino-2-hydroxybenzaldehyde N,N-diphenylhydrazone. 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 (in 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 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. filtrationCrystals were filtered off
  13. washwashed with cold ethanol
  14. customto be 95.5–96.5° C.
  15. customrecrystallized from a mixture of 2-propanol and ether in a 10:1 ratio by volume)
  16. customAn elemental analysis yielded the
  17. customfollowing results in weight percent

출처 및 근거

ORD 기록
ord-0c929fbbf01746f49fd4d57183aac439
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179574B2

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