Sodium Carbonate → 2-Chloroquinazoline

Participants

Reaction Steps

A portion of the quinazolinone (4.46 gm, 0.02 moles) was refluxed in phosphorous oxychloride (20 mL) for one hour. After cooling, the solution was carefully poured into cold 20% sodium carbonate solution (500 mL). The solid chloroquinazoline was isolated by filtration, washed with water and dissolved in methylene chloride (400 mL). The solution was dried over magnesium sulfate, filtered and stripped to give the chloroquinazoline as a pale yellow solid in a yield of 3.7 gm, 76.5%. The 4-chloroquinazoline (3.7 gm, 0.015 moles) was refluxed in ethanol with N-2-aminoethylmorpholine (3.99 gm, 0.031 moles) for one hour. Once cooled, the solution was stripped and the residue was dissolved in water (400 mL). The solution was made basic by the addition of sodium carbonate and the product was extracted into methylene chloride (2×100 mL). The combined extracts were washed with water (50 mL) and were then dried over magnesium sulfate. After filtration, the extracts were stripped to give the product as a tan solid. The solid was recrystallized from ethyl acetate (25 mL) and hexane (50 mL). The product, 203-93 was isolated as an off white solid in a yield of 2.86 gm, 56.0%.

Provenance & Evidence