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

HRID 240797Notes

Reaction equation

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

Participants

Reactant 2

HCID 12152Benzyl azide

HCID 621176Ethynyltributyltin

Product 1

HCID 689891381-benzyl-4-(tributylstannyl)-1H-1,2,3-triazole

Procedure

Ethynyltributylstannane (1 mL, 3.4 mmol) and benzyl azide (0.65 mL, 5.2 mmol) were heated to 130° C. for 24 hours. The mixture was adsorbed onto silica gel, and purified by silica gel chromatography eluting with 1:4 ethyl acetate:hexanes to afford the title compound.

Workup

custompurified by silica gel chromatography
washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record: ord-2cf326be26c44c51a15a50805ee623cf
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648069B2

Reaction notes

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