Sodium Azide → HCID 22122227, compound

HRID 1859173Notes

Reaction equation

HRID 1859173 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])[C:6](=[O:21])[C:5]1=[O:22].[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O>[N:23]([CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])[C:6](=[O:21])[C:5]1=[O:22])=[N+:24]=[N-:25]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22122230HCID 22122230, compound

Product 1

HCID 22122227HCID 22122227, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4.5 g of 1-(2-bromoethyl)-4-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine, 1.03 g of sodium azide and 45 ml of N,N-dimethylformamide was stirred at 80° C. for 1 hour and then distilled under reduced pressure to remove the solvent. To the resulting residue were added 60 ml of ethyl acetate and 30 ml of water, and the pH was adjusted to 3 with 2N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with two 30-ml portions 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. After the solvent was distilled off under reduced pressure, 5 ml of diisopropyl ether and 5 ml of diethyl ether were added to the resulting residue and the crystals were collected by filtration to obtain 3.7 g of 1-(2-azidoethyl)-4-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine as colorless crystals.

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. additionTo the resulting residue were added 60 ml of ethyl acetate and 30 ml of water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with two 30-ml portions of ethyl acetate
  6. washThe combined organic layer was washed with 20 ml of water
  7. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  8. distillationAfter the solvent was distilled off under reduced pressure, 5 ml of diisopropyl ether and 5 ml of diethyl ether
  9. additionwere added to the resulting residue
  10. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-7cf20e3902e14b28871df749c2aa9ef7
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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