Benzylacetylene → 5-benzyl-1-(2,3-dichlorophenyl)-1H-1,2,3-triazole

HRID 2232965Notes

Reaction equation

HRID 2232965 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[Cl:11])=[N+:2]=[N-:3].[C:12]1([CH2:18][C:19]#[CH:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[CH2:18]([C:19]1[N:1]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=2[Cl:11])[N:2]=[N:3][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 575753BenzylacetyleneHCID 126814021-Azido-2,3-dichlorobenzene

Product 1

HCID 444404305-benzyl-1-(2,3-dichlorophenyl)-1H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1-Azido-2,3-dichlorobenzene (200 mg, 1.06 mmol) (Cambie J. Organomet. Chem. 1996, 507, 1) and 3-phenyl-1-propyne (150 μL, 1.1 equiv) were combined in toluene (0.2 mL) and heated at 100° C. for 18 hours, allowed to cool to room temperature, and then concentrated under reduced pressure to give a mixture of regioisomers. The residue was purified by flash chromatography eluting with hexanes:ethyl acetate (3:1) to provide the title compound. MS (DCI/NH3) m/z 304 (M+H)+; 1H NMR (CDCl3) δ 3.87 (br s, 2H), 6.98 (m, 2H), 7.13 (dd, 1H), 7.22 (m, 3H), 7.29 (t, 1H), 7.56 (s, 1H), 7.64 (dd, 1H).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto give
  4. additiona mixture of regioisomers
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexanes:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-0be92175c61c40bd869f9932747f0eed
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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