(1S,2S)-1,2-diphenylethane-1,2-diamine → N,N'-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-(1S,2S)-1,2-diphenylethylenediamine

HRID 1292552

반응식

HRID 1292552 반응식
[C:1]1([C@H:7]([NH2:16])[C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]([CH:19]([C:31](=[O:33])[CH3:32])[C:20]([C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30])=[O:21])=O>C(O)C.ClCCl.CCOCC.CCCCCC>[O:33]=[C:31]([CH3:32])[CH:19]([C:20](=[O:21])[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30])[CH:17]=[N:16][C@@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[N:9]=[CH:17][CH:19]([C:20](=[O:21])[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30])[C:31](=[O:33])[CH3:32]

참가 물질

5

반응물 2

HCID 6931238(1S,2S)-1,2-diphenylethane-1,2-diamineHCID 189157562-Formyl-(2,4,6-trimethylphenyl)-1,3-dioxobutane

생성물 1

HCID 86752666N,N'-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-(1S,2S)-1,2-diphenylethylenediamine수율 71%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 21850893Dichloromethane ether hexane용매

실험 절차

In 70 ml of ethanol was dissolved 1.06 g (5 mmol) of (S,S)-1,2-diphenylethylenediamine. In a nitrogen atmosphere and at room temperature, 30 ml of an ethanol solution containing 2.32 g (10.5 mmol) of 2-formyl-(2,4,6-trimethylphenyl)-1,3-dioxobutane was added to the solution, which was stirred for 2 hours at room temperature. The reaction mixture was then heated to 50° C. and reaction took place in 2 hours. After the completion of reaction, the solvent was distilled off in vacuum, obtaining a crude product. The crude product was dissolved in dichloromethane/ether/hexane for recrystallization, obtaining 2.28 g (isolation yield 71%) of an optically active ligand (N,N'-bis[3-oxo-2-(2,4,6-trimethylbenzoyl)butylidene]-(1S,2S)-1,2-diphenylethylenediamine) as white crystals. The thus obtained optically active ligand was analyzed by 1H-NMR, IR, and elemental analysis and measured for melting point and specific rotatory power. The results are shown below.

후처리

  1. additionwas added to the solution, which
  2. temperatureThe reaction mixture was then heated to 50° C.
  3. customreaction
  4. customin 2 hours
  5. customAfter the completion of reaction
  6. distillationthe solvent was distilled off in vacuum
  7. customobtaining a crude product

출처 및 근거

ORD 기록
ord-343eb5588b0d472983981067a741ecde
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756790

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