Dimethylformamide → 1-Octadecyl-2,5-pyrrolidinedione

HRID 634602Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[C:20]1(=[O:26])[NH:24][C:23](=[O:25])[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>[I-].[K+].O>[CH2:2]([N:24]1[C:20](=[O:26])[CH2:21][CH2:22][C:23]1=[O:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

In a 500 ml flask equipped with a stirrer and a condenser were charged 30.6 g of 1-bromoctadecane, 10.0 g of succinimide, 13.9 g of potassium carbonate, 0.5 g of potassium iodide and 60 ml of DMF, and the mixture was stirred on an oil bath at 100° C. After cooling the reaction mixture to room temperature, it was poured into a large amount of distilled water, and the precipitated crystals were collected by filtration under reduced pressure and washed with distilled water. The residue was recrystallized from IPA to obtain 28.5 g of the title compound. Melting point: 76° C.

Workup

customIn a 500 ml flask equipped with a stirrer and a condenser
temperatureAfter cooling the reaction mixture to room temperature
filtrationthe precipitated crystals were collected by filtration under reduced pressure
washwashed with distilled water
customThe residue was recrystallized from IPA

Sources & evidence

ORD record: ord-f574728485c34d349a6f1cca2f192e20
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184180B2

Reaction notes

Loading…