Water → 7-bromo-2-methoxyquinazolin-4(3H)-one

HRID 1473663Notes

Reaction equation

HRID 1473663 reaction equation
[CH3:1][O:2][C:3]([NH2:5])=[NH:4].Cl.[Br:7][C:8]1[CH:9]=[C:10]2NC(=O)O[C:12](=[O:13])[C:11]2=[CH:18][CH:19]=1.[O-]CC.[Na+].O>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:11]([C:12](=[O:13])[NH:4][C:3]([O:2][CH3:1])=[N:5]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 3083899Carbamimidic acid, methyl ester, hydrochloride (1:1)HCID 115215774-Bromoisatoic anhydride

Product 1

HCID 1364090737-bromo-2-methoxyquinazolin-4(3H)-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of o-methylisourea hydrochloride (1.256 g, 11.36 mmol) and 4-bromoisatoic anhydride (2.500 g, 10.33 mmol) in 10 mL DMF was treated with sodium ethoxide (1.476 g, 21.69 mmol) and was allowed to stir at room temperature overnight. LC/MS showed mostly product, so the reaction mixture was poured into water and the resulting solid was filtered and dried yielding 7-bromo-2-methoxyquinazolin-4(3H)-one (2.57 g, 10.08 mmol, 98% yield) with impurities. (M+H)+=255.0.

Workup

  1. filtrationthe resulting solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-89dd9e44714646748a118c4c144932a9
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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