Reaction #607468

Reaction equation

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

thionyl chloride

chloroform

→

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

Yield 32.8%

Solvents

hexane

Conditions

Workup

1. 1
   TemperatureThe reaction medium was heated
2. 2
   Temperatureto reflux
3. 3
   Otherthe reaction, which
4. 4
   workup.ADDITIONwere added
5. 5
   Otherto precipitate the product
6. 6
   Filtrationfiltered
7. 7
   Washwashed with two portions of hexane
8. 8
   Otherdried

Procedure

2-ethyl-3-(2-hydroxyethyl)quinazoline-4 (3H)-one (5.00 g; 22.91 mmol) and thionyl chloride (1.672 mL, 22.91 mmol) were added to a 150 mL reactor, together with 60 mL of chloroform. The reaction medium was heated to reflux and for completing the reaction, which was accompanied through CG/MS. After the end of the reaction, 100 mL of hexane were added and the solution was agitated at room temperature in order to precipitate the product. The resulting suspension was vacuum filtered, washed with two portions of hexane and dried, yielding 3-(2-chloroethyl)-2-ethylquinazoline-4 (3H)-one as a white solid (1.78 g; 7.52 mmol; yield: 32.8%).

Source