Benzyl azide → 2-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde

HRID 1040403

Reaction equation

HRID 1040403 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])#[CH:2].[CH2:11]([N:18]=[N+:19]=[N-:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O.O>[CH2:11]([N:18]1[CH:2]=[C:1]([C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[CH:5]=[O:6])[N:20]=[N:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:11]([N:18]1[C:1]([C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[CH:5]=[O:6])=[CH:2][N:20]=[N:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 12152Benzyl azideHCID 6403682-Ethynylbenzaldehyde

Product 2

HCID 866524202-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehydeYield 65%HCID 866524212-(1-benzyl-1H-1,2,3-triazol-5-yl)benzaldehydeYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-ethynylbenzaldehyde (200 mg, 1.54 mmol) and benzyl azide (0.38 mL, 3.0 mmol) in 2.0 mL of N,N-dimethylformamide was stirred at 80° C. overnight. The reaction mixture was diluted with water, and the solution was extracted with a 5:1 solution (12 mL) of ethyl acetate and hexane. The extract was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain 2-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde (259 mg, 65%) and 2-(1-benzyl-1H-1,2,3-triazol-5-yl)benzaldehyde (118 mg, 30%).

Workup

  1. extractionthe solution was extracted with a 5:1 solution (12 mL) of ethyl acetate and hexane
  2. washThe extract was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40)

Sources & evidence

ORD record
ord-5f6252eb299946e0bd73a3877ad94ae8
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Linked notes

Loading…