Reaktion #4610

Reaktionsgleichung

N-(2-nitrobenzoyl)-N'-[3-chloro-4-(5-chloro-2-pyrimidinyloxy)phenyl]urea

2,5-dichloropyrimidine

4-amino-2-chlorophenol

potassium carbonate

→

3-chloro-4-(5-chloro-2-pyrimidinyloxy)aniline

Lösungsmittel

dimethylsulfoxide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereacted in a nitrogen atmosphere at 100° C. for 1.5 hours
2. 2
   SonstigeAfter the completion of the reaction
3. 3
   Extraktionextracted with diethyl ether
4. 4
   WaschenThe extract was washed with a saturated sodium chloride aqueous solution
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   SonstigeThe crude product thereby obtained
8. 8
   Sonstigewas purified
9. 9
   Sonstigeisolated by silica gel column chromatography

Vorschrift

N-(2-nitrobenzoyl)-N'-[3-chloro-4-(5-chloro-2-pyrimidinyloxy)phenyl]urea (1) Into a flask, 1.50 g of 2,5-dichloropyrimidine, 1.45 g of 4-amino-2-chlorophenol, 2.76 g of potassium carbonate and 15 ml of dimethylsulfoxide, were introduced, and reacted in a nitrogen atmosphere at 100° C. for 1.5 hours under stirring. After the completion of the reaction, the product was poured into water, and extracted with diethyl ether. The extract was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The crude product thereby obtained was purified and isolated by silica gel column chromatography to obtain 2.20 g of 3-chloro-4-(5-chloro-2-pyrimidinyloxy)aniline having a melting point of from 95 to 96° C.

Quelle