Ethyl 2-oxocyclohexanecarboxylate → 2-(Trifluoromethyl)-5,6,7,8-tetrahydroquinazolin-4-ol

HRID 2254117Notes

Reaction equation

HRID 2254117 reaction equation
[Na].[C:2]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=O)([O:4]CC)=O.[F:14][C:15]([F:20])([F:19])[C:16]([NH2:18])=[NH:17]>C(O)C>[F:14][C:15]([F:20])([F:19])[C:16]1[NH:18][C:2](=[O:4])[C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:17]=1

Participants

5

Reactant 3

HCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 2776882TrifluoroacetamidineHCID 5360545Sodium2×

Product 1

HCID 1357422392-(Trifluoromethyl)-5,6,7,8-tetrahydroquinazolin-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 10 mL of absolute ethanol under a nitrogen atmosphere was added 0.15 g of sodium metal. After all the sodium had reacted, 1.00 g of 2-carboethoxycyclohexanone was added followed by 0.78 g of 85% trifluoroacetamidine. The reaction was refluxed gently overnight. The reaction was cooled to room temperature and all solvents were removed by evaporation. The pH of the residue was adjusted to 6 with dilute hydrochloric acid and refluxed briefly and allowed to cool. The resulting solid was collected. (0.73 g, 57%): 1H NMR (DMSO-d6, 300 MHz) δ 13.0 (s, 1H), 2.78 (m, 2H), 2.45 (m, 2H), 1.78 (m, 4H).

Workup

  1. temperatureThe reaction was refluxed gently overnight
  2. customall solvents were removed by evaporation
  3. temperaturerefluxed briefly
  4. temperatureto cool
  5. customThe resulting solid was collected

Sources & evidence

ORD record
ord-3923e92eda1b4fc594cf61e4093b8da7
Source dataset
uspto-grants-1993_08
Patent number
US05234936

Reaction notes

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