4-Morpholinobenzaldehyde → Ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate

HRID 1595367노트

반응식

HRID 1595367 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9](=[N:15]O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.C([O-])(=O)C.[NH4+:36]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:36][C:28]([C:27]3[CH:30]=[CH:31][C:24]([N:21]4[CH2:22][CH2:23][O:18][CH2:19][CH2:20]4)=[CH:25][CH:26]=3)=[N:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 2913494-MorpholinobenzaldehydeHCID 517165Ammonium AcetateHCID 178472894HCID 178472894, 화합물

생성물 1

HCID 178470196Ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate수율 24.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Ethyl 3-(4-chlorophenyl)-2-hydroxyimino-3-oxopropionate (200 g), 4-morpholinobenzaldehyde (244.4 g) and ammonium acetate (603 g) were refluxed under heating for 15 hr in acetic acid, and the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform (2 L), and the solution was neutralized with a saturated aqueous hydrogencarbonate solution and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after drying, the solvent was evaporated under reduced pressure and crude crystals were obtained from ethyl acetate. The crude crystals were subjected to silica gel column chromatography to give the objective ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate (78 g), melting point 215° C.

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform (2 L)
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customafter drying
  6. customthe solvent was evaporated under reduced pressure
  7. customcrude crystals were obtained from ethyl acetate

출처 및 근거

ORD 기록
ord-3ff0c9e84cce40eca2cca31ea61478fd
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288061B1

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