Water → 8-Carbamoyl-2-(2-ethoxyphenyl)quinazolin-4(3H)-one

HRID 374776Notes

Reaction equation

HRID 374776 reaction equation
[C:1]([C:4]1[C:5]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH3:23])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=[O:8])(=[O:3])[NH2:2].[OH-].[Na+].O>C(O)C>[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]2[C:5]=1[N:13]=[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][CH3:23])[NH:9][C:7]2=[O:8])(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 185365653-Carbamoyl-2-(2-ethoxybenzamido)benzamide

Product 1

HCID 1357149148-Carbamoyl-2-(2-ethoxyphenyl)quinazolin-4(3H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 3-carbamoyl-2-(2-ethoxybenzamido)benzamide (Preparation 18; 1 g, 0,003 mol) sodium hydroxide (0.61 g, 0.015 mol), water (30 ml) and ethanol (7 ml) was heated under reflux for 1 hour. The cool solution was washed with dichloromethane (3×30 ml), acidified to pH 1 with 2N hydrochloric acid and the resulting precipitate collected by filtration. The solid was suspended in saturated aqueous sodium carbonate solution (60 ml) and this suspension extracted with dichloromethane-methanol (98: 2, 3×100 ml). The extracts were combined, dried (Na2SO4) and evaporated under vacuum, then the residue triturated with diethyl ether (50 ml) to give the title compound as a white solid (0.72 g, 78%), m.p. 252°-254° C. Found: C,66.28; H,4.97; N,13.65. C17H15H3O3 requires C,66.01; H,4.89; N,13.59%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. washThe cool solution was washed with dichloromethane (3×30 ml)
  4. filtrationthe resulting precipitate collected by filtration
  5. extractionthis suspension extracted with dichloromethane-methanol (98: 2, 3×100 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated under vacuum
  8. customthe residue triturated with diethyl ether (50 ml)

Sources & evidence

ORD record
ord-0d57679428024db9b112e482519ef32a
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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