Ethanol → HCID 13533643, compound

HRID 464126Notes

Reaction equation

HRID 464126 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[CH2:9]([O:11][C:12](=[O:20])[CH2:13][C:14]([C:16]([F:19])([F:18])[F:17])=O)[CH3:10].C([O-])(=O)C.[NH4+:25].C(O)C.[CH3:29][N:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH:35]=O>>[CH2:9]([O:11][C:12]([C:13]1[CH:35]([C:31]2[N:30]([CH3:29])[CH:34]=[CH:33][N:32]=2)[C:2]2[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=2[NH:25][C:14]=1[C:16]([F:19])([F:18])[F:17])=[O:20])[CH3:10]

Participants

6

Reactant 5

HCID 702EthanolHCID 104341,3-CyclohexanedioneHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 13533643HCID 13533643, compoundYield 7%

Procedure

To a stirred mixture of 2.3 g (0.02 mole) of 1,3-cyclohexandione, ethyl-4,4,4-trifluoroacetoacetate (3.3 g, 0.02 mole) and ammonium acetate (4.9 g, 0.4 mole) in 50 mL of absolute ethanol, (2.0 g, 0.02 mole) of N-methylimidazole-2-carboxaldehyde was added. The reaction mixture was refluxed for 24 hours and allowed to cool to room temperature. The solvent was evaporated in vacuo, and the residue was separated by high performance liquid chromatography (30% methanol-ethylacetate mixture as the eluent) to afford 0.5 g (7% yield ) of the title compound, m.p. 197°-198° C.; MS, m/e 369 (M+); NMR (CDCl3) δ1.0 (t, 3 H, CCH3), 1.5-2.4 (m, 6 H, cyclohexenone), 3.7 (s, 3 H, NCH3), 4-4.1 (q, 2 H, CH2C), 5.0 (s, 1 H, dihydropyridine-H), 6.5 (d, 1 H, imidazole-H), 6.8 (d, 1 H, imidazole-H) and 9.6 (s, 1 H, NH).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 24 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was separated by high performance liquid chromatography (30% methanol-ethylacetate mixture as the eluent)

Sources & evidence

ORD record
ord-eacabaceac2e47e9a56c2d53b3e929ef
Source dataset
uspto-grants-1985_10
Patent number
US04546186

Reaction notes

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