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

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

Reactant 4

HCID 7061N,N-Diethylaniline

HCID 8857Ethyl Acetate

HCID 24387Phosphorus trichloride

HCID 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.