Phosphorus oxychloride → 7-Bromo-4-chloro-2-methylquinazoline

HRID 1271217Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:16])=O>CN(C)C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:16])=[N:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 0.45 g (1.87 mmol) of 7-bromo-2-methyl-3H-quinazolin-4-one in 0.48 ml N,N-dimethylaniline was treated with 1.41 ml (15.4 mmol) phosphorous oxychloride and heated at 60° C. for 2 h. The reaction mixture was evaporated in vacuo and the residue taken up in 20 ml water, neutralized with 10 ml saturated aqueous sodium bicarbonate and twice extracted with 25 ml dichloromethane. The organic layer is washed with 25 ml water, 25 ml brine, dried over magnesium sulfate and evaporated in vacuo. The residue is purified by chromatography on silica gel with heptane/ethylacetate (2:1) to give 0.29 g (59%) of 7-bromo-4-chloro-2-methyl-quinazoline as an orange solid. Mp. >82° C. EI mass spectrum, m/e: 258 (M calculated for C9H6BrClN2: 258).

Workup

customThe reaction mixture was evaporated in vacuo
extractiontwice extracted with 25 ml dichloromethane
washThe organic layer is washed with 25 ml water, 25 ml brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue is purified by chromatography on silica gel with heptane/ethylacetate (2:1)

Sources & evidence

ORD record: ord-e9a5f005bd4f4cc18c9c6347c15f37f2
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07205309B2

Reaction notes

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