N,N-Diethylaniline → 4-Chloro-5-nitro-6-ethylpyrimidine

HRID 129469Notes

Reaction equation

HRID 129469 reaction equation
CCN(C1C=CC=CC=1)CC.O[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([CH2:22][CH3:23])[N:16]=[CH:15][N:14]=1.C(OCC)(=O)C.P(Cl)(Cl)[Cl:31]>>[Cl:31][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([CH2:22][CH3:23])[N:16]=[CH:15][N:14]=1

Participants

5

Reactant 4

HCID 7061N,N-DiethylanilineHCID 8857Ethyl AcetateHCID 24387Phosphorus trichlorideHCID 178437745HCID 178437745, compound

Product 1

HCID 193717294-Chloro-5-nitro-6-ethylpyrimidine

Conditions

Temperature
60 °C

Procedure

18.7 g (0.125 mol) of diethylaniline are dissolved in 18 ml of phosphorus chloride, and then 8.46 g (0.05 mol) of 4-hydroxy-5-nitro-6-ethylpyrimidine are stirred in. During the addition, the temperature rises from 22° to 47° C. A solution is formed which is heated at 60° C. for 2 hours. It is then stirred with ice-water and ethyl acetate for 30 minutes for the purpose of hydrolysis. The organic phase is separated off and combined with the extracts obtained by extraction, and the mixture is washed with NaHCO3 solution. Removal of the solvent yields 9.1 g of crude product, which is purified by column chromatography on silica gel (eluant:ethyl acetate/hexane 20:80 parts). 6.76 g (72.1% of the theoretical yield) of pure product are obtained in the form of an oil.

Workup

  1. additionDuring the addition
  2. customrises from 22° to 47° C
  3. customA solution is formed which
  4. customThe organic phase is separated off
  5. customobtained by extraction
  6. washthe mixture is washed with NaHCO3 solution
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-dd2d483ddd3848d0a51cb0cc84f50dc8
Source dataset
uspto-grants-1995_11
Patent number
US05468751

Reaction notes

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