Ethanol → 2-(2-Ethoxyphenyl)-8-methoxyquinazolin-4(3H)-one

HRID 412034Notes

Reaction equation

HRID 412034 reaction equation
[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([NH:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].OO.C(O)C>ClCCl.O>[CH2:1]([O:3][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]1[NH:13][C:11](=[O:12])[C:10]2[C:9](=[C:17]([O:18][CH3:19])[CH:16]=[CH:15][CH:14]=2)[N:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 185365662-(Ethoxybenzamido)-3-methoxybenzamide

Product 1

HCID 1359665132-(2-Ethoxyphenyl)-8-methoxyquinazolin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 2-(2-ethoxybenzamido)-3-methoxybenzamide (2.6 g, 0.0083 mol), anhydrous potassium carbonate (2.33 g, 0.017 mol), hydrogen peroxide (30%, 4 ml), ethanol (40 ml) and water (80 ml) was heated under reflux for 1 hour. The mixture was allowed to cool and poured into a mixture of water (200 ml) and dichloromethane (100 ml), then the aqueous phase separated, acidified to pH 4 by the addition of 2N hydrochloric acid and extracted with dichloromethane (2×100 ml). The organic solutions were combined, dried (MgSO4) and evaporated under vacuum to give the title compound, which crystallized from ethyl acetate as a colourless solid (2.8 g, 83%), m.p. 198-199° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool
  4. customthe aqueous phase separated
  5. additionacidified to pH 4 by the addition of 2N hydrochloric acid
  6. extractionextracted with dichloromethane (2×100 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-f497be3c5dfb49b6af9f54e6bf664c69
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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