Benzyl azide → 1-Benzyl-5-o-tolyl-4-(tributylstannyl)-1H-1,2,3-triazole

HRID 240771Notes

Reaction equation

HRID 240771 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9])#[CH:2].[CH2:10]([Sn:14]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])N(C)C)[CH2:11][CH2:12][CH3:13].[CH2:26]([N:33]=[N+:34]=[N-:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([N:33]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:9])=[C:2]([Sn:14]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])[N:35]=[N:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 12152Benzyl azideHCID 1365982-MethylphenylacetyleneHCID 11034994Dimethylaminotri-n-butyltin

Product 1

HCID 689903221-Benzyl-5-o-tolyl-4-(tributylstannyl)-1H-1,2,3-triazole

Conditions

Temperature
70 °C

Procedure

2-Ethynyl toluene (456 μL, 3.62 mmol) was added to 1,1,1-tributyl-N,N-dimethylstannanamine (1.21 g, 3.62 mmol), and the mixture was stirred in a sealed vial at 70° C. for 3 hours. The mixture was cooled to ambient temperature, and the vial was stirred unsealed for 10 minutes. Benzyl azide (678 μL, 5.42 mmol) was added, and the vial was resealed and heated to 130° C. overnight. The mixture was purified by silica gel chromatography eluting with a gradient of 5-45% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 539.8 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringthe vial was stirred unsealed for 10 minutes
  3. temperatureheated to 130° C. overnight
  4. customThe mixture was purified by silica gel chromatography
  5. washeluting with a gradient of 5-45% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-db41fc845266421baee24a8370fff188
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

Loading…