(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

Reaction equation

HRID 1292552 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 21850893Dichloromethane ether hexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-343eb5588b0d472983981067a741ecde
Source dataset
uspto-grants-1998_05
Patent number
US05756790

Linked notes

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