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

HRID 576847Notes

Reaction equation

HRID 576847 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-e1ca3158c2374876abbc5704b5169ab8
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

Loading…