Reaction #607460

Reaction equation

thionyl chloride

3-(2-hydroxyethyl)quinazoline-4 (3H)-one

→

3-(2-chloroethyl) quinazoline-4 (3H)-one

Yield 82.0%

Solvents

water

Conditions

Workup

1. 1
   Otherforming a white suspension
2. 2
   workup.WAITThe reaction medium was kept at this temperature under agitation for thirty minutes
3. 3
   workup.WAITafter which it was left
4. 4
   Temperatureto cool to about 40° C
5. 5
   Otherforming a pinkish suspension, which
6. 6
   Filtrationvacuum filtered
7. 7
   Washwashed with three portions of 10 mL of an ethanol/water mixture (50% v/v)

Procedure

This thionyl chloride (1,095 mL, 15 mmol) was added to 3-(2-hydroxyethyl)quinazoline-4 (3H)-one (2.0 g, 10.52 mmol) in a reactor, forming a white suspension that heated spontaneously to 85° C. The reaction medium was kept at this temperature under agitation for thirty minutes, after which it was left to cool to about 40° C. Next, 50 mL of water was added, forming a pinkish suspension, which was kept under agitation for two hours. The product was then vacuum filtered and washed with three portions of 10 mL of an ethanol/water mixture (50% v/v), yielding 3-(2-chloroethyl) quinazoline-4 (3H)-one as a pale white solid (1.8 g, 8.63 mmol, yield=82%).

Source