Benzyl azide → 1-benzyl-5-(2-naphthyl)-1H-1,2,3-triazole

HRID 387402Notes

Reaction equation

HRID 387402 reaction equation
[CH2:1]([N:8]=[N+:9]=[N-:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)#[CH:12]>C[C-]1C(C)=C(C)C(C)=C1C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru+].C1C=CC=CC=1>[CH2:1]([N:8]1[C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:12][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12152Benzyl azideHCID 1150172-Ethynylnaphthalene

Product 1

HCID 161292761-benzyl-5-(2-naphthyl)-1H-1,2,3-triazole

Reagents, catalysts & solvents 2

HCID 71310463Chlororuthenium(1+) 1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-ide--triphenylphosphane (1/1/2)CatalystHCID 241BenzeneSolvent

Procedure

Benzyl azide (0.400 g, 3.00 mmol), 2-ethynylnaphthalene (0.503 g, 3.31 mmol), Cp*RuCl(PPh3)2 (25 mg, 0.031 mmol). Solvent, benzene; reaction temperature, 80° C.; reaction time, 4 hours; yield, 0.80 g (93%). EI-MS: m/z 285 [M+].

Workup

  1. customreaction temperature, 80° C.
  2. customreaction time, 4 hours
  3. customyield

Sources & evidence

ORD record
ord-529bfa8def8340d3aa9b4c31393a54b2
Source dataset
uspto-grants-2013_02
Patent number
US08372986B2

Reaction notes

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