Cyclohexyl bromide → HCID 83874985, compound
Reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1C=O.[C:8](=[O:11])([O-])[O-].[Na+].[Na+].[CH:14]1(Br)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C=O)C>[CH:14]1([N:3]2[CH:4]=[C:5]([CH:8]=[O:11])[N:1]=[CH:2]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of imidazolecarboxaldehyde (60 mg, 0.63 mmol) in DMF (0.4 mL) was added sodium carbonate (132 mg, 1.26 mmol). The mixture was then treated with a solution of cyclohexylbromide (152 mg, 0.94 mmol) in DMF (0.4 mL) dropwise and stirred at 90° C. for 72 h. The reaction mixture was partitioned between EtOAc (2 mL) and water (2 mL), and the aqueous layer was extracted with EtOAc. The organic layers were combined, dried with Na2SO4, filtered, and concentrated to yield to yield the title compound which was used without further purification (66 mg). (m/z): [M+H]+ calcd for C10H14N2O 179.11; found, 179.2.
Workup
- customThe reaction mixture was partitioned between EtOAc (2 mL) and water (2 mL)
- extractionthe aqueous layer was extracted with EtOAc
- dry with materialdried with Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto yield
Sources & evidence
- ORD record
- ord-a8e3bf741206415d92d52ed9a3126ded
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211894B2
Reaction notes
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