Benzyl Chloride → 1-benzyl-2-nitro-1H-imidazole

HRID 1189881Notes

Reaction equation

HRID 1189881 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:9]([C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)([O-:11])=[O:10].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:13]1[CH:14]=[CH:15][N:16]=[C:12]1[N+:9]([O-:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 107012-Nitroimidazole

Product 1

HCID 3311201-benzyl-2-nitro-1H-imidazoleYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzyl chloride (1.8 mL, 15.4 mmol, 1.2 equiv) was added to a solution of 2-nitroimidazole (1.45 g, 12.8 mmol) and triethylamine (3.6 mL, 25.7 mmol, 2 equiv) in DCM (40 mL). The reaction mixture was stirred at reflux for 72 h, allowed to cool to rt, diluted with DCM, washed with H2O and brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 7:3) to afford 1.31 g of the title compound as a white solid: ES-MS: 204.0 [M+H]+; tR=3.72 min (System 1); TLC: Rf=0.22 (Hex/EtOAc, 7:3).

Workup

  1. temperatureat reflux for 72 h
  2. washwashed with H2O and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 7:3)

Sources & evidence

ORD record
ord-953eb4a4b2334f2086ff4ab58bcd2f99
Source dataset
uspto-grants-2014_03
Patent number
US08674099B2

Reaction notes

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