4-Nitrophenol → 4-Chloro-6-(4-nitrophenoxy)pyrimidine

HRID 387697Notes

Reaction equation

HRID 387697 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([O-:11])=[O:10].[H-].[Na+]>CN(C)C=O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([O:18][C:15]2[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidineYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

After adding 4,6-dichloropyrimidine (750 mg) to a suspension of 4-nitrophenol (700 mg) and sodium hydride (60%) (200 mg) in dimethylformamide (13 ml) at 0° C., the mixture was heated and stirred at 80° C. for 1.5 hours. The reaction solution was poured into saturated saline and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated. The obtained residue was passed through an NH silica gel column (Fuji Silicia Chemical), eluted with a solvent (ethyl acetate-hexane=1-4) and concentrated to obtain 700 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. additionThe reaction solution was poured into saturated saline
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with a solvent (ethyl acetate-hexane=1-4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4b05ff42b3244187a5c870f705426fd7
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

Loading…