Phosphorus oxychloride → HCID 136174441, compound

HRID 354819Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]2[C:6]([C:7](=[O:16])[NH:8][C:9](=O)[NH:10]2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:9]1[NH:8][C:7](=[O:16])[C:6]2[C:11](=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 123200177,8-Dimethoxyquinazoline-2,4(1H,3H)-dione

Product 1

HCID 136174441HCID 136174441, compound

Procedure

Equimolar amounts (0.10 mole) of 7,8-dimethoxy-2,4-(1H,3H)-quinazolinedione and phosphorous oxychloride are stirred at room temperature overnight and the volatiles evaporated in vacuo to afford a residue of 2-chloro-7,8-dimethoxy-4(3H)-quinazolineone which is purified by washing with aqueous sodium bicarbonate, extraction with chloroform and evaporation of solvent. To the residue is added a solution of 0.10 mole of 3-methylpiperidine in 300 ml. of isoamyl alcohol and the mixture heated at reflux for three hours, the solvent is then evaporated in vacuo to afford 2-(3-methylpiperidin-1-yl)-7,8-dimethoxy-4(3H)-quinazolineone hydrochloride. To this is added 150 ml. of phosphorous oxychloride and the resulting mixture is heated at reflux for two hours. The liquids are evaporated to give a residue of 2-(3-methylpiperidin-1-yl)-4-chloro-7,8-dimethoxyquinazoline hydrochloride. The product is dissolved in dilute aqueous sodium bicarbonate, extracted with chloroform, dried (Na2SO4) and the solvent evaporated.

Workup

customthe volatiles evaporated in vacuo

Sources & evidence

ORD record: ord-77f243abe7454a2db4067ab836ae74a0
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04377581

Reaction notes

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