Acetic Anhydride → 1,1'-(cyclohexane-1,3-diylbis(methylene))bis(1H-pyrrole-2,5-dione)

HRID 1468581

Reaction equation

HRID 1468581 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]1([CH2:16][NH2:17])[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH2:15])[CH2:9]1.[C:18]([O-:21])(=O)[CH3:19].[Na+].[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[CH:8]1([CH2:16][N:17]2[C:1](=[O:7])[CH:2]=[CH:3][C:4]2=[O:5])[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]2[C:18](=[O:21])[CH:19]=[CH:24][C:23]2=[O:25])[CH2:9]1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 174061,3-Bis(aminomethyl)cyclohexaneHCID 517045Sodium Acetate

Product 1

HCID 190780031,1'-(cyclohexane-1,3-diylbis(methylene))bis(1H-pyrrole-2,5-dione)

Procedure

The general procedure was carried out using maleic anhydride (20.59 g, 210 mmol), 1,3-cyclohexanebis(methylamine) (14.22 g, 100 mmol), sodium acetate (1.64 g, 20 mmol), and acetic anhydride (22.46 g, 220 mmol). The resulting compound was purified by column chromatography (98:2 DCM:EtOAc), and the product obtained as a white solid (3.55 g/12%).

Workup

  1. customThe resulting compound was purified by column chromatography (98:2 DCM:EtOAc)
  2. customthe product obtained as a white solid (3.55 g/12%)

Sources & evidence

ORD record
ord-486a53ba1d4d4be38c0454c55122c699
Source dataset
uspto-grants-2015_04
Patent number
US09005708B2

Linked notes

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