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

HRID 240764

Reaction equation

HRID 240764 reaction equation
[CH2:1]([Sn:5]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:9][CH2:10][CH2:11][CH3:12])[C:6]#[C:7][CH3:8])[CH2:2][CH2:3][CH3:4].[CH2:17]([N:24]=[N+:25]=[N-:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([N:24]1[C:7]([CH3:8])=[C:6]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH3:12])[N:26]=[N:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 12152Benzyl azideHCID 2733165Tributyl(prop-1-yn-1-yl)stannane

Product 1

HCID 689903421-Benzyl-5-methyl-4-(tributylstannyl)-1H-1,2,3-triazole

Conditions

Temperature
150 °C

Procedure

Tributyl(1-propynyl)tin (3.87 g, 11.8 mmol) and benzyl azide (2.2 mL, 17.6 mmol) were combined and heated to 150° C. overnight. The mixture was purified by silica gel chromatography eluting with a gradient of 5-40% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 464.2 (M+H)+.

Workup

  1. customThe mixture was purified by silica gel chromatography
  2. washeluting with a gradient of 5-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b4ca326d8b7d43b6a5b90edc7a946609
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Linked notes

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