Dimethyl Sulfoxide → 4-(5-Bromo-2-pyrimidinyloxy)-3-chloroaniline

HRID 4512

Reaction equation

HRID 4512 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:16][C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][C:12]=2[Cl:17])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 775784-Amino-2-chlorophenolHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 137714404-(5-Bromo-2-pyrimidinyloxy)-3-chloroanilineYield 62.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a flask, 7.00 g of 5-bromo-2-chloropyrimidine, 5.19 g of 4-amino-2-chlorophenol, 9.98 g of potassium carbonate and 70 ml of dimethylsulfoxide were introduced, and reacted in a nitrogen atmosphere at 120° C. for 1.5 hours under stirring. After the completion of the reaction, the product was poured into water, and extracted with ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and then purified by silica gel column chromatography, whereby 6.80 g of oily 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline was obtained.

Workup

  1. customreacted in a nitrogen atmosphere at 120° C. for 1.5 hours
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-21579b9c6dbe424cb126459426052c6c
Source dataset
uspto-grants-1988_02
Patent number
US04727077

Linked notes

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