Imidazole → 1-(2-chloro-4-nitrophenyl)-1H-imidazole

HRID 1670487Notes

Reaction equation

HRID 1670487 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 74431,2-Dichloro-4-nitrobenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 53053741-(2-chloro-4-nitrophenyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.0 g (5.21 mmol) of 3,4-dichloronitrobenzene (Fluka, Buchs, Switzerland), 532 mg (7.81 mmol) imidazole (Aldrich, Buchs, Switzerland) and 1.35 g (10.4 mmol) Hünig's base in 4 ml of DMA are heated in a microwave oven at 180° C. for 1 h 40 min. The reaction mixture is quenched with sat. aqueous NaHCO3 and extracted with EtOAc (2×). The organic layers is washed with sat. aqueous NaHCO3 (3×), with brine, dried over MgSO4, filtered and evaporated. The residue is purified by flash chromatography on silica gel (CH2Cl2-MeOH 1:0 to 93:7) to provide the title compound as an oil. ES-MS: 224 (M+H)+; analytical HPLC: tret=2.11 minutes (Grad 1).

Workup

  1. customThe reaction mixture is quenched with sat. aqueous NaHCO3
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layers is washed with sat. aqueous NaHCO3 (3×), with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by flash chromatography on silica gel (CH2Cl2-MeOH 1:0 to 93:7)

Sources & evidence

ORD record
ord-eaca35b621034eb7866e66f923bf8bfb
Source dataset
uspto-grants-2011_08
Patent number
US07994170B2

Reaction notes

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