Acetic Anhydride → 1H-Pyrrole-2,5-dione, 1,1'-(1,8-octanediyl)bis-

HRID 1468580Notes

Reaction equation

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

Participants

Reactant 4

HCID 7918Acetic Anhydride

HCID 7923Maleic Anhydride

HCID 242501,8-Octanediamine

HCID 517045Sodium Acetate

Product 1

HCID 5735371H-Pyrrole-2,5-dione, 1,1'-(1,8-octanediyl)bis-

Procedure

The general procedure was carried out using maleic anhydride (14.27 g, 146 mmol), 1,8-octanediamine (10.0 g, 69.3 mmol), sodium acetate (1.14 g, 13.9 mmol) and acetic anhydride (15.57 g, 153 mmol). The resulting compound was purified by column chromatography (98:2 DCM:EtOAc), and the product obtained as a white solid (5.2 g/25%).

Workup

customThe resulting compound was purified by column chromatography (98:2 DCM:EtOAc)
customthe product obtained as a white solid (5.2 g/25%)

Sources & evidence

ORD record: ord-de61101344e5432eb50062cb0957331d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09005708B2

Reaction notes

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