2-Methyl-N-[4-[(2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]phenyl]benzamide → 5-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1291648노트

반응식

HRID 1291648 반응식
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].O=[C:8]1[C:14]2C=CC=[CH:18][C:13]=2[N:12]([C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:22][CH:21]=2)[CH2:11][CH2:10][CH2:9]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:1]=[C:2]1[C:5]2[CH:14]=[CH:8][CH:9]=[CH:10][C:11]=2[N:12]([C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:22][CH:21]=2)[CH2:13][CH2:18][CH2:3]1

참가 물질

5

반응물 2

HCID 108108812-Methyl-N-[4-[(2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]phenyl]benzamideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 196080415-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine수율 84.2%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매

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온도
-5 °C

실험 절차

Methyltriphenylphosphonium bromide (4.30 g) is suspended in tetrahydrofuran (100 ml) and thereto is added potassium t-butoxide (1.58 g) under ice-cooling. The mixture is stirred at -5° C. for 1 hour and thereto is added 5-oxo-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.60 g) and the mixture is stirred at room temperature for 1 hour. The reaction solution is poured into ice-water (200 ml) and extracted with ethyl acetate. The extract is washed with saturated saline solution and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:2), and recrystallized from ethyl acetate/n-hexane to give 5-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.34 g) as white powder, m.p. 216°-217° C.

후처리

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:2)
  8. customrecrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-0bd0cda93b1841af86326b4357d51112
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753677

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