Acetic Acid → 2-Cyclohexyl-5-ethylpyridine
Reaction equation
[CH2:1]([CH:3]([CH:6]=O)[CH:4]=O)[CH3:2].C1([NH:14]C(NC2C=CC=CC=2)=O)C=CC=CC=1.[CH:24]1([C:30]([CH3:32])=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(O)(=O)C.C([O-])(=O)C.[NH4+].ClS(O)(=O)=O.[OH-].[Na+]>CC(O)C>[CH2:1]([C:3]1[CH:6]=[CH:32][C:30]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:14][CH:4]=1)[CH3:2]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 1
Procedure
8.71 g (87 mmol) of 2-ethylmalonaldehyde, 16.8 g (79 mmol) of 1,3-diphenylurea, 10.0 g (79 mmol) of methyl cyclohexyl ketone, 11.9 ml (198 mmol) of acetic acid and 39 g (500 mmol) of ammonium acetate were dissolved in 160 ml of 2-propanol, and 5.3 g (39.5 mmol) of chlorosulfonic acid was added dropwise thereto at room temperature. The reaction solution was allowed to undergo the reaction at 80° C. for 2 hours. After completion of the reaction, this was cooled to room temperature, neutralized with 200 g (1.2 mol) of 25% sodium hydroxide aqueous solution and then extracted three times with 200 ml of toluene. The organic layer was concentrated and then purified by distillation under a reduced pressure to obtain 10.8 g (yield 72%) of the title compound (purity 99.3%, melting point 79-81° C.).
Workup
- customat room temperature
- customthe reaction at 80° C. for 2 hours
- customAfter completion of the reaction
- extractionextracted three times with 200 ml of toluene
- concentrationThe organic layer was concentrated
- distillationpurified by distillation under a reduced pressure
Sources & evidence
- ORD record
- ord-627d2d7f766b481d94ec5ac97836a9a1
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723522B2
Reaction notes
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