Thionyl Chloride → 2-Chloropyrimidine-4-carbonyl chloride

HRID 232902Notes

Reaction equation

HRID 232902 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([Cl:13])=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 221357512-Chloropyrimidine-4-carboxylic acid

Product 1

HCID 450814902-Chloropyrimidine-4-carbonyl chlorideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

12 drops of dimethylformamide was added to a solution of 3.0 g (18.9 mmol) of 2-chloropyrimidine-4-carboxylic acid in 60 ml of thionyl chloride. The reaction was then refluxed for 6 hours. After cooling to room temperature, excess thionyl chloride was removed on a rotary evaporator and the residue distilled (boiling point approximately 100° C./1 mbar). 2.95 g of product, corresponding to a yield of 88 percent relative to the 2-chloropyrimidine-4-carboxylic acid used, which crystallized in the receiving flask, was obtained. The melting point of the product was 52.2° to 53.1° C. Other data for the product was:

Workup

  1. temperatureThe reaction was then refluxed for 6 hours
  2. customexcess thionyl chloride was removed on a rotary evaporator
  3. distillationthe residue distilled (boiling point approximately 100° C./1 mbar)
  4. customwhich crystallized in the receiving flask
  5. customwas obtained
  6. customwas 52.2° to 53.1° C

Sources & evidence

ORD record
ord-51b9d9b4febb4d03ad70e843905f1c95
Source dataset
uspto-grants-1997_01
Patent number
US05591853

Reaction notes

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