Magnesium → HCID 178478019, compound

HRID 2097681Notes

Reaction equation

HRID 2097681 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:12]=1.[Mg]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][NH:11][CH:12]=1

Participants

5

Reactant 2

HCID 5462224MagnesiumHCID 58501886HCID 58501886, compound

Product 1

HCID 178478019HCID 178478019, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (17) (1 equiv) in dry MeOH (0.1 M) was added to magnesium powder (10 equiv) under argon at 0° C. and the resulting suspension was stirred at 0° C. for 1 hour, diluted with DCM (3 volumes) and quenched very slowly with 10% HCl (15 ml). The layers were separated and the organic one was washed with 5% aqueous sodium bicarbonate solution and brine, dried (MgSO4), filtered and concentrated in vacuo. An oil was obtained which was purified by flash chromatography (Hex/AcOEt 5:1 and 1:1) to render 4-(2-chlorophenyl)-1H-1,2,3-triazole (18) as a white crystalline solid (42% yield).

Workup

  1. customquenched very slowly with 10% HCl (15 ml)
  2. customThe layers were separated
  3. washthe organic one was washed with 5% aqueous sodium bicarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customAn oil was obtained which
  8. customwas purified by flash chromatography (Hex/AcOEt 5:1 and 1:1)

Sources & evidence

ORD record
ord-002e99575eaa4c87a55a332e2ca2b302
Source dataset
uspto-grants-2013_05
Patent number
US08450350B2

Reaction notes

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