Potassium Carbonate → 3-Chloro-4-[(5-chloropyrimidin-2-yl)oxy]aniline

HRID 4514

Reaction equation

HRID 4514 reaction equation
[N+](C1C=CC=CC=1C(NC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[N:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=2)=[C:14]([Cl:26])[CH:13]=1)=O)=O)([O-])=O.ClC1N=CC(Cl)=CN=1.NC1C=CC(O)=C(Cl)C=1.C(=O)([O-])[O-].[K+].[K+]>O.CS(C)=O>[Cl:26][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[O:18][C:19]1[N:20]=[CH:21][C:22]([Cl:25])=[CH:23][N:24]=1)[NH2:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 775784-Amino-2-chlorophenolHCID 5906412,5-DichloropyrimidineHCID 13771441N-(2-nitrobenzoyl)-N'-[3-chloro-4-(5-chloro-2-pyrimidinyloxy)phenyl]urea

Product 1

HCID 140970913-Chloro-4-[(5-chloropyrimidin-2-yl)oxy]aniline

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

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.

Workup

  1. customreacted in a nitrogen atmosphere at 100° C. for 1.5 hours
  2. customAfter the completion of the reaction
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe crude product thereby obtained
  8. customwas purified
  9. customisolated by silica gel column chromatography

Sources & evidence

ORD record
ord-9d1b517cc1984e3fb05e9d6f78f2916e
Source dataset
uspto-grants-1988_02
Patent number
US04727077

Linked notes

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