Bis-(1H-imidazol-2-YL)-methanone → 7-methoxy-3,4-dihydro-1H-quinazolin-2-one

HRID 655657Notes

Reaction equation

HRID 655657 reaction equation
[NH2:1][CH2:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].[C:12](C1NC=CN=1)(C1NC=CN=1)=[O:13]>C1COCC1>[CH3:11][O:10][C:7]1[CH:6]=[C:4]2[C:3]([CH2:2][NH:1][C:12](=[O:13])[NH:5]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 536307282-Aminomethyl-5-methoxyaniline

Product 1

HCID 536307277-methoxy-3,4-dihydro-1H-quinazolin-2-oneYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-aminomethyl-5-methoxyaniline (1.2 g. 7.9 mmol) and carbonyl diimidazole (1.53 g, 9.5 mmol) were added to THF (100 ml) and the mixture was stirred at room temperature overnight. The insoluble matter precipitated was obtained by filtration, washed with dichloromethane and water, dried to obtain 7-methoxy-3,4-dihydro-1H-quinazolin-2-one (1.11 g) as white powder.

Workup

  1. customThe insoluble matter precipitated
  2. customwas obtained by filtration
  3. washwashed with dichloromethane and water
  4. customdried

Sources & evidence

ORD record
ord-07732181713145559f8a2f63b8c9d11d
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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