1,2-Dibromoethane → HCID 22122230, compound

HRID 1859172Notes

Reaction equation

HRID 1859172 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C:7]1=[O:13].[H-].[Na+].[Br:22][CH2:23][CH2:24]Br>CN(C)C=O>[Br:22][CH2:23][CH2:24][N:9]1[CH2:10][CH2:11][N:6]([CH2:5][C:4]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:3]=2[O:2][CH3:1])[C:7](=[O:13])[C:8]1=[O:12]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 127069801-[(2,4-Dimethoxyphenyl)methyl]piperazine-2,3-dione

Product 1

HCID 22122230HCID 22122230, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In 100 ml of N,N-dimethylformamide was suspended 10 g of 1-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine, and 1.67 g of sodium hydride (60%, oil) was added to the suspension, followed by stirring at 50° C. for 1 hour. Then, the reaction mixture was cooled to room temperature, after which 16.5 ml of 1,2-dibromoethane was added thereto and the resulting mixture was stirred at the same temperature for 4 hours. After the solvent was distilled off under reduced pressure, a mixed solvent of 100 ml of ethyl acetate and 60 ml of water was added to the residue and the pH was adjusted to 3 with 2N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with 50 ml of ethyl acetate. The combined organic layer was washed with 20 ml of water and then a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=30:1) to obtain 6.1 g of 1-(2-bromoethyl)-4-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine as colorless crystals.

Workup

  1. additionwas added to the suspension
  2. temperatureThen, the reaction mixture was cooled to room temperature
  3. stirringthe resulting mixture was stirred at the same temperature for 4 hours
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. additiona mixed solvent of 100 ml of ethyl acetate and 60 ml of water was added to the residue
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with 50 ml of ethyl acetate
  8. washThe combined organic layer was washed with 20 ml of water
  9. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-351e9fd191ff49d88d14a93f08ed5fa7
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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