Sodium Chloride → 2,4-Dichloro-6-methylpyrimidine

HRID 224485Notes

Reaction equation

HRID 224485 reaction equation
O[C:2]1[N:7]=[C:6](O)[CH:5]=[C:4]([CH3:9])[N:3]=1.P(Cl)(Cl)([Cl:12])=O.CCN(C1C=CC=CC=1)CC.[OH-].[Na+].[Na+].[Cl-:29]>>[Cl:29][C:2]1[N:7]=[C:6]([Cl:12])[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 7061N,N-DiethylanilineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride2×HCID 178429421HCID 178429421, compound

Product 1

HCID 794712,4-Dichloro-6-methylpyrimidine

Procedure

45 g (0.36 M) of 2,4-dihydroxy-6-methyl-pyrimidine have been treated with phosphorous oxychloride in the presence of diethylaniline. After having been refluxed during 3 hours the reaction mixture was cooled and the excess of phosphorous oxychloride was decomposed over ice, then the mixture was neutralized with NaOH, saturated with a NaCl solution and extracted with ether. By separation and evaporation of the ethereal extracts there was obtained a residue which was distilled to yield 57 g of the title compound at B.p. 99°/11 Torr.

Workup

  1. temperatureAfter having been refluxed during 3 hours the reaction mixture
  2. temperaturewas cooled
  3. extractionextracted with ether
  4. customBy separation and evaporation of the ethereal extracts
  5. customthere was obtained a residue which
  6. distillationwas distilled

Sources & evidence

ORD record
ord-e92caac2ce404b7390d07a54c74e9177
Source dataset
uspto-grants-1980_11
Patent number
US04232156

Reaction notes

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