Benzyl azide → 4-(1-benzyl-1H-1,2,3-triazol-5-yl)benzaldehyde

HRID 387405Notes

Reaction equation

HRID 387405 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:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][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:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][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 27716454-Ethynylbenzaldehyde

Product 1

HCID 116805234-(1-benzyl-1H-1,2,3-triazol-5-yl)benzaldehyde

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 (0.200 g, 1.50 mmol), 4-ethynylbenzaldehyde (0.200 g, 1.54 mmol), Cp*RuCl(PPh3)2 (25 mg, 0.031 mmol). Solvent, benzene; reaction temperature, 80° C.; reaction time, 2 hours; yield, 0.32 g (81%). EI-MS: m/z 264 [M+1].

Workup

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

Sources & evidence

ORD record
ord-f8cb6781f79b4e22a85b531c4ad50dd2
Source dataset
uspto-grants-2013_02
Patent number
US08372986B2

Reaction notes

Loading…