Azobisisobutyronitrile → N-vinyl-2-pyrrolidinone dibutyl maleate

HRID 648360Notes

Reaction equation

[CH:1]([N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])=[CH2:2].[C:9]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:19])/[CH:10]=[CH:11]\[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13].C1C(C(OOC(C)(C)C)=O)=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C(C)=CC=CC=1>[CH:1]([N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])=[CH2:2].[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:13])/[CH:11]=[CH:10]\[C:9]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19]

Participants

Conditions

Temperature: 140 °C

Procedure

N-vinyl-2-pyrrolidinone (32 g, 0.29 mole) and dibutyl maleate (68 g, 0.29 mole) were dissolved in 400 ml of xylene in a reaction vessel and the temperature was increased to 90° C. t-Butyl perbenzoate (1 g, 0.005 mole) and azobisisobutyronitrile (2 g, 0.012 mole) were added slowly to the xylene solution over two hours. The reaction was carried out in a nitrogen atmosphere. The temperature was increased to 140° C. for one hour and then the reaction was allowed to cool to room temperature. The xylene was evaporated in a vacuum, leaving a reddish orange oil residue. This oil was purified by dissolving it in boiling heptane, from which it separated upon cooling as a viscous, orange liquid: ##STR13## Anal. calcd. for C18H29O5N: C, 63.69; H, 8.61; N, 4.12. Found: C, 63.64; H, 8.59; N, 4.25. Residual N-vinyl-2-pyrrolidinone, as measured by gas/liquid chromatography (GLC), was 1.0 ±0.1%.

Workup

temperatureto cool to room temperature
customThe xylene was evaporated in a vacuum
customleaving a reddish orange oil residue
customThis oil was purified
dissolutionby dissolving it
customfrom which it separated
temperatureupon cooling as a viscous, orange liquid

Sources & evidence

ORD record: ord-c53a8da0f7c949998266dc9b66b6e404
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04412014

Reaction notes

Loading…