Reaction #4610

Reaction equation

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

Solvents

dimethylsulfoxide

water

Conditions

Workup

1. 1
   Otherreacted in a nitrogen atmosphere at 100° C. for 1.5 hours
2. 2
   OtherAfter the completion of the reaction
3. 3
   Extractionextracted with diethyl ether
4. 4
   WashThe extract was washed with a saturated sodium chloride aqueous solution
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   OtherThe crude product thereby obtained
8. 8
   Otherwas purified
9. 9
   Otherisolated by silica gel column chromatography

Procedure

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.

Source