1-Pent-4-ynyl-1H-[1,2,3]triazole → 1-(2-Methyl-3-phenyl-allyl)-4-(3-[1,2,3]triazol-1-yl-propyl)-1H-[1,2,3]triazole

HRID 384185Notes

Reaction equation

HRID 384185 reaction equation
[CH2:1]([N:6]1[CH:10]=[CH:9][N:8]=[N:7]1)[CH2:2][CH2:3][C:4]#[CH:5].[N:11]([CH2:14][C:15]([CH3:23])=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N+:12]=[N-:13]>>[CH3:23][C:15](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:14][N:11]1[CH:5]=[C:4]([CH2:3][CH2:2][CH2:1][N:6]2[CH:10]=[CH:9][N:8]=[N:7]2)[N:13]=[N:12]1

Participants

3

Reactant 2

HCID 579144081-Pent-4-ynyl-1H-[1,2,3]triazoleHCID 76639733(3-Azido-2-methylpropenyl)-benzene

Product 1

HCID 670640821-(2-Methyl-3-phenyl-allyl)-4-(3-[1,2,3]triazol-1-yl-propyl)-1H-[1,2,3]triazoleYield 99.6%

Procedure

1-Pent-4-ynyl-1H-[1,2,3]triazole (0.100 g, 0.739 mmol) was reacted with (3-Azido-2-methylpropenyl)-benzene (0.154 g, 0.889 mmol) following the general procedure for click reactions outlined above to produce 1-(2-Methyl-3-phenyl-allyl)-4-(3-[1,2,3]triazol-1-yl-propyl)-1H-[1,2,3]triazole (0.227 g, Quantitative) as a white solid. 1H NMR (300 MHz, DMSO) δ 7.91 (s, 1H), δ 7.77 (s, 2H), δ 7.40-7.25 (m, 5H), δ 6.47 (s, 1H), δ 5.05 (s, 2H), δ 4.48 (t, 2H), δ 2.62 (t, 2H), δ 2.50 (t, 2H), δ 2.21 (m, 2H), δ 1.74 (s, 3H) ppm; 13C (75 MHz, DMSO) δ 146.4, 137.1, 134.8, 133.6, 132.8, 129.4, 129.3, 129.2, 128.9, 127.6, 123.0, 57.9, 54.0, 32.9, 29.6, 22.7, 16.2 ppm; HRMS (ESI) calcd for C17H21N6(M+) 309.1822, found 309.1821.

Sources & evidence

ORD record
ord-e33598c43d954228b368ec749f3d7ca1
Source dataset
uspto-grants-2013_02
Patent number
US08367713B2

Reaction notes

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