2-(Benzylthio)-8-ethoxy-5,6-dihydroquinazoline → 2-(benzylthio)-6,7-dihydroquinazolin-8(5H)-one

HRID 875122

Reaction equation

HRID 875122 reaction equation
[CH2:1]([S:8][C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH:13]=[C:12]([O:19]CC)[C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O>[CH2:1]([S:8][C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][C:12](=[O:19])[C:11]=2[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 574441122-(Benzylthio)-8-ethoxy-5,6-dihydroquinazoline

Product 1

HCID 574441132-(benzylthio)-6,7-dihydroquinazolin-8(5H)-oneYield 74%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1.5 g (5 mmol) of 2-(benzylthio)-8-ethoxy-5,6-dihydroquinazoline were dissolved in 50 mL of acetic acid and 3 mL of water. The solution was stirred at refluxing temperature for 4 hours. The solvent was then removed under vacuum, the residue partitioned between dichloromethane and a NaHCO3 saturated solution. The organic layer was dried over anhydrous Na2SO4 and concentrated, giving 1.0 g (74% yield) of the title compound.

Workup

  1. temperatureat refluxing temperature for 4 hours
  2. customThe solvent was then removed under vacuum
  3. customthe residue partitioned between dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1719f120f0114d8ea6700fbf508e3516
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Linked notes

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