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

HRID 2409759Notes

Reaction equation

HRID 2409759 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-d50ef5100a544371868977c3c2c3df36
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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