Potassium Carbonate → Methyl 4-(2-cyclohexyl-1H-imidazol-1-yl)-2-methoxy-5-nitrobenzoate

HRID 72760Notes

Reaction equation

HRID 72760 reaction equation
F[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:15][CH3:16])[CH:3]=1.[CH:17]1([C:23]2[NH:24][CH:25]=[CH:26][N:27]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>C(OCC)(=O)C.O>[CH:17]1([C:23]2[N:27]([C:2]3[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:15][CH3:16])[CH:3]=3)[CH:26]=[CH:25][N:24]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 10014029Methyl 4-fluoro-2-methoxy-5-nitrobenzoateHCID 111594052-Cyclohexyl-1H-imidazole

Product 1

HCID 59198783Methyl 4-(2-cyclohexyl-1H-imidazol-1-yl)-2-methoxy-5-nitrobenzoateYield 100.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-fluoro-2-methoxy-5-nitrobenzoate 8.57 g, 2-cyclohexylimidazole 5.61 g, potassium carbonate 10.34 g and N,N-dimethylacetamide 75 mL was heated at 100° C. for 5 hours in nitrogen atmosphere. The reaction liquid was diluted with ethyl acetate, poured in water and the organic layer was separated. The organic layer was washed with brine, dried over magnesium sulfate and removed of the solvent by distillation to provide 13.52 g of the title compound.

Workup

  1. customThe reaction liquid
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customremoved of the solvent by distillation

Sources & evidence

ORD record
ord-de22b31a02844f109f0cd72d5ac10fa0
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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