Potassium Iodide → 2-Azido-N-(beta-oxo-2,5-dimethoxy phenehyl)acetamide

HRID 10909Notes

Reaction equation

HRID 10909 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][C:7](=[O:18])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[O:16][CH3:17])=[O:4].[N-:19]=[N+:20]=[N-:21].[Na+].[I-].[K+]>CC(C)=O>[N:19]([CH2:2][C:3]([NH:5][CH2:6][C:7](=[O:18])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[O:16][CH3:17])=[O:4])=[N+:20]=[N-:21]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 33557Sodium AzideHCID 116376042-Chloro-N-(b-oxo-2,5-dimethoxy-phenylethyl)-acetamid

Product 1

HCID 115726752-Azido-N-(beta-oxo-2,5-dimethoxy phenehyl)acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

In a four neck round bottomed flask, 45 gm (0.165 mole) of 2-Chloro-N-(β-oxo-2,5-Dimethoxy phenethyl)-acetamide prepared according to step (b), 27 g (0.415 mole) sodium azide and 8.3 g (0.049 mole) potassium iodide and 900 ml of acetone is charged. The solution is refluxed at 60° C. for 5 hours. After completion of the reaction the reaction mass cooled and filtered to remove inorganics. Acetone is distilled off under atmospheric pressure. Water is added and the resulting yellow lumps are filtered. (Yield: 91%). The solid is recrystallized from methanol. The following physical properties are measured.

Workup

  1. additionis charged
  2. customAfter completion of the reaction the reaction mass
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove inorganics
  6. distillationAcetone is distilled off under atmospheric pressure
  7. additionWater is added
  8. filtrationthe resulting yellow lumps are filtered
  9. customThe solid is recrystallized from methanol

Sources & evidence

ORD record
ord-8c23ebe7c2534221923202bb5e04eb41
Source dataset
uspto-grants-2006_08
Patent number
US07094928B2

Reaction notes

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