Hydrogen Peroxide → 4-(2-Azidoethyl)benzamide

HRID 1071971Notes

Reaction equation

HRID 1071971 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)=[N+:2]=[N-:3].C([O-])([O-])=[O:15].[K+].[K+].OO>CO.O>[N:1]([CH2:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]([NH2:11])=[O:15])=[CH:8][CH:7]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 22390712HCID 22390712, compound

Product 1

HCID 223906894-(2-Azidoethyl)benzamideYield 96%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2-azidoethyl)benzonitrile (1.0 g, 5.81 mmol) in a 5:1 mixture of MeOH/H2O (100 mL), K2CO3 (4.41 g. 31.94 mmol) was added and the resulting solution cooled to 0° C. Then 15.4 mL of a 30% H2O2 solution was added and the reaction was allowed to warm to room temperature. After stirring at room temperature for approximately three hours, the crude reaction mixture was concentrated under reduced pressure to remove MeOH and then extracted with EtOAc (3×100 mL). Combined organics were dried over sodium sulfate, filtered, and concentrated in vacua. Crude product was subjected to silica gel purification eluting with 1% MeOH in CH2Cl2 to give 1.06 g (96%) of 4-(2-azidoethyl)benzamide.

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. customthe crude reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customto remove MeOH
  6. extractionextracted with EtOAc (3×100 mL)
  7. dry with materialCombined organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacua
  10. customCrude product was subjected to silica gel purification
  11. washeluting with 1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-6d4cc4f453954841ac15f5d7dc10e492
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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