Sodium Azide → 5-(1-Azido-2-ethylbutyl)-1-(4-fluorobenzyl)-1H-1,2,4-triazole

HRID 748058Notes

Reaction equation

HRID 748058 reaction equation
[CH2:1]([CH:3]([CH2:19][CH3:20])[CH:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:9]=[CH:8][N:7]=1)O)[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C.O>[N:21]([CH:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:9]=[CH:8][N:7]=1)[CH:3]([CH2:19][CH3:20])[CH2:1][CH3:2])=[N+:22]=[N-:23]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 685941182-Ethyl-1-[1-(4-fluorobenzyl)-1H-1,2,4-triazol-5-yl]butan-1-ol

Product 1

HCID 866000065-(1-Azido-2-ethylbutyl)-1-(4-fluorobenzyl)-1H-1,2,4-triazoleYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-ethyl-1-[1-(4-fluorobenzyl)-1H-1,2,4-triazol-5-yl]butan-1-ol (0.459 g, 1.42 mmol) in DMF (10 mL) was added sodium azide (0.277 g, 4.26 mmol) and the mixture was heated to reflux for 3 h. After cooling, the reaction mixture was diluted with H2O and extracted with EtOAc twice. The organic extracts were dried (MgSO4), filtered, concentrated in vacuo and purified by column chromatography (SiO2, EtOAc/hexane, 1:9) to yield a clear oil in 67% yield.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc twice
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography (SiO2, EtOAc/hexane, 1:9)
  9. customto yield a clear oil in 67% yield

Sources & evidence

ORD record
ord-215cd51e624a4dfcb4564181ab2ce61f
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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