Potassium Carbonate → 1-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carbonitrile

HRID 475708Notes

Reaction equation

HRID 475708 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]#[N:7])[N:3]=[CH:2]1.F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[O:18][CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:19][O:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[N:1]1[CH:5]=[C:4]([C:6]#[N:7])[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 144519681-Fluoro-2-methoxy-4-nitrobenzeneHCID 178510437HCID 178510437, compound

Product 1

HCID 667083621-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carbonitrileYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-Imidazole-4-carbonitrile (300 mg, 3.22 mmol) and 4-Fluoro-3-methoxynitrobenzene (552 mg, 3.22 mmol) in DMF (Volume: 6446 μl) was added K2CO3 (891 mg, 6.45 mmol). The resulting mixture was brought to 120° C. and stirred overnight. The reaction mixture was diluted with EtOAc (20 mL), washed with water (2×10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated in vacuo to give 1-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carbonitrile (698 mg, 2.86 mmol, 89% yield). LC-MS (M+H)+=245.0. 1H NMR (500 MHz, MeOD) δ ppm 8.30-8.34 (1H), 8.19-8.23 (1H), 8.09-8.12 (1H), 8.00-8.05 (1H), 7.71-7.79 (1H), 4.02-4.10 (3H).

Workup

  1. customwas brought to 120° C.
  2. washwashed with water (2×10 mL), brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d744649519ff497b9e78decf2aee86c3
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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