Dimethylformamide → 1-Octadecyl-2,5-pyrrolidinedione

HRID 398748Notes

Reaction equation

HRID 398748 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)C=O>[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

7

Reactant 4

HCID 6228DimethylformamideHCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 11439Succinimide

Product 1

HCID 181838581-Octadecyl-2,5-pyrrolidinedione

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

30.6 Grams of bromooctadecane, 10.0 g of succinimide, 13.9 g of potassium carbonate, 0.5 g of potassium iodide and 60 ml of N,N-dimethylformamide (DMF) were charged in a flask equipped with a stirrer and a condenser and stirred with heating on an oil bath of 100° C. for 2 hours. The reaction mixture was cooled to room temperature and introduced into a large amount of pure water. The precipitated crystal was filtered off under reduced pressure and washed with methanol. The crystal was recrystallized from 2-propanol to obtain 28.5 g of the desired product. m.p. 75.8° C.

Workup

  1. customequipped with a stirrer and a condenser
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationThe precipitated crystal was filtered off under reduced pressure
  4. washwashed with methanol
  5. customThe crystal was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-46f13101ef0c4d7388f7e68d2b1ce702
Source dataset
uspto-grants-1998_10
Patent number
US05817599

Reaction notes

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