Sodium hydride → HCID 12707041, compound

HRID 1462629Notes

Reaction equation

HRID 1462629 reaction equation
[H-].[Na+].[CH2:3]([N:9]1[CH2:14][CH2:13][NH:12][C:11](=[O:15])[C:10]1=[O:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)([O-:19])=[O:18]>CN(C=O)C>[CH2:3]([N:9]1[CH2:14][CH2:13][N:12]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)[C:11](=[O:15])[C:10]1=[O:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 12542705HCID 12542705, compound

Product 1

HCID 12707041HCID 12707041, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With 1.1 g of sodium hydride (50% purity) was mixed 50 ml of DMF, and 4.6 g of 1-n-hexyl-2,3-dioxopiperazine was added thereto with stirring at room temperature over a period of 10 minutes. Subsequently, the resulting mixture was subjected to reaction at 50° to 60° C. for 30 minutes, and 5.5 g of p-nitrobenzyl bromide was added to the reaction mixture over a period of 10 minutes, after which the mixture thus obtained was further subjected to reaction at 50° to 60° C. for 2 hours. The solvent was removed by distillation under reduced pressure. The residue was extracted with 70 ml of ethyl acetate, and the ethyl acetate layer was washed with water and then a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The crystals thus obtained were recrystallized from isopropyl alcohol to obtain 4.0 g (51.9% yield) of 1-n-hexyl-4-(4-nitrobenzyl)-2,3-dioxopiperazine having a melting point of 115° to 117° C.

Workup

  1. additionwas added
  2. customSubsequently, the resulting mixture was subjected to reaction at 50° to 60° C. for 30 minutes
  3. customafter which the mixture thus obtained
  4. customwas further subjected to reaction at 50° to 60° C. for 2 hours
  5. customThe solvent was removed by distillation under reduced pressure
  6. extractionThe residue was extracted with 70 ml of ethyl acetate
  7. washthe ethyl acetate layer was washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  9. customafter which the solvent was removed by distillation under reduced pressure
  10. customThe crystals thus obtained
  11. customwere recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-db20fbff9f274dfd904984f37b7ae96c
Source dataset
uspto-grants-1984_07
Patent number
US04460774

Reaction notes

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