Water → 4-Chloro-6,7-dimethoxyquinazoline

Participants

Reaction Steps

A 6,7-dimethoxyquinazolin-4(3H)-one suspension (2a) (0.79 g, 3.83 mmol) in thionyl chloride (7.0 mL) containing 10 drops of N,N-dimethylformarnide (DMF) was agitated and heated under reflux for three hours, until a solution was obtained. The reaction mixture was left cooling at room temperature. The reaction environment was diluted in dichloromethane and water (160 mL) and left in ice bath. The material was treated under agitation with 30 mL of saturated Na2CO3 solution. Na2CO3 was carefully added until pH was adjusted to 7-8 range. Then, the aqueous phase was extracted with CH2Cl2 (2×30 mL), and the organic phase compound was washed with salt solution (2×10 mL), dried over magnesium sulfate, filtered, and the solvent was evaporated in a rotatory evaporator in order to provide 6,7-dimethoxy-4-chloroquinazoline (3a) as a yellow solid (0.68 g, 3.03 mmol, 79%), which was used without purification in the next stage: melting point 185-187° C.

Provenance & Evidence