Thionyl Chloride → 4-Chloro-7-methoxyquinazolin-6-yl acetate

HRID 403662Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][NH:9][C:8]2=O)(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>CN(C=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[Cl:20])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate (8.7 g, 0.037 mol), thionyl chloride (120 ml, 1.65 mol) and DMF (1 ml) was stirred and heated to 55° C. for 6 hours. The mixture was cooled to room temperature and thionyl chloride was evaporated. The solid was dissolved in chloroform and the solution was washed with sodium bicarbonate and brine, the chloroform was evaporated under reduced pressure to give 7.9 g of a gray product. MS (ESI) m/z: 253 (M+1).

Workup

temperatureThe mixture was cooled to room temperature
customthionyl chloride was evaporated
dissolutionThe solid was dissolved in chloroform
washthe solution was washed with sodium bicarbonate and brine
customthe chloroform was evaporated under reduced pressure

Sources & evidence

ORD record: ord-d8530beba4094308b604546e3b5b5acf
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748453B2

Reaction notes

Loading…