Acetamidine monohydrochloride → 4(3H)-Quinazolinone, 5,6,7,8-tetrahydro-2-methyl-

HRID 2254121Notes

Reaction equation

HRID 2254121 reaction equation
[Na].[C:2]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=O)([O:4]CC)=O.Cl.[C:15]([NH2:18])(=[NH:17])[CH3:16]>C(O)C>[CH3:16][C:15]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 67170Acetamidine monohydrochlorideHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 5360545Sodium2×

Product 1

HCID 1354312714(3H)-Quinazolinone, 5,6,7,8-tetrahydro-2-methyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 50 mL of absolute ethanol under a nitrogen atmosphere was added 5.65 g of sodium metal. After all the sodium had reacted, 20.15 g of 2-carboethoxycyclohexanone was added followed by 14.50 g of acetamidine hydrochloride. 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. Successive crops of solid were collected by concentration of the mother liquors (13.1 g, 65%): 1H NMR (DMSO-d6, 300 MHz) δ 12.18 (s, 1H), 2.22 (m, 2H), 2.15 (m, 2H), 2.10 (s, 3H), 1.65 (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
  6. customSuccessive crops of solid were collected by concentration of the mother liquors (13.1 g, 65%)

Sources & evidence

ORD record
ord-cea4143fd0a549ca9cc802f0ef1d994f
Source dataset
uspto-grants-1993_08
Patent number
US05234936

Reaction notes

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