Reaction #336843

Reaction equation

hydrochloric acid

sodium hydroxide

diethyl oxalacetate sodium salt

4-Chlorobenzenecarboximidamide monohydrochloride

→

title compound

Yield 45.0%

2-(4-chlorophenyl)-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid

Yield 45.0%

Solvents

water

Conditions

Workup

1. 1
   workup.DISSOLUTIONAfter 1 h the solids had dissolved
2. 2
   workup.ADDITIONwas slowly added (causing foaming) until the pH
3. 3
   OtherThe solid was isolated by filtration
4. 4
   Washwashed with water and methanol
5. 5
   OtherThe solid was then triturated twice with hot methanol
6. 6
   Washwashed repeatedly with 1 N hydrochloric acid
7. 7
   Dryingonce with methanol and dried

Procedure

To a mixture of diethyl oxalacetate sodium salt (123.2 g, 586 mmol) in water (750 mL) was slowly added aqueous sodium hydroxide (50%, 47 g, 586 mmol). After 1 h the solids had dissolved. 4-Chlorobenzenecarboximidamide monohydrochloride (111.95 g, 586 mmol) was then added, and the mixture was heated at 70° C. overnight. After cooling to room temperature concentrated hydrochloric acid was slowly added (causing foaming) until the pH was lowered to 1.5. The solid was isolated by filtration and washed with water and methanol. The solid was then triturated twice with hot methanol, washed repeatedly with 1 N hydrochloric acid, then once with methanol and dried to afford the title compound (66.07 g).

Source