Thionyl Chloride → 5-Chloro-2-(methylsulfanyl)pyrimidine-4-carbonyl chloride

HRID 2206842Notes

Reaction equation

HRID 2206842 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([OH:12])=O)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.S(Cl)([Cl:15])=O>CN(C)C=O.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:10]([Cl:15])=[O:12])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 7257115-Chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid

Product 1

HCID 140671885-Chloro-2-(methylsulfanyl)pyrimidine-4-carbonyl chlorideYield 91.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

With stirring, 15 g of 5-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid were added a little at a time to 40.8 g (25 ml, 0.34 mol) of thionyl chloride and 0.47 g (0.5 ml, 6.5 mmol) of N,N-dimethylformamide, and the reaction mixture was then heated under reflux until a marked evolution of gas was no longer noticeable. The mixture is taken up in a little methylene chloride. Concentration gives 15 g of 5-chloro-2-(methylsulfanyl)pyrimidine-4-carbonyl chloride, which was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureunder reflux until a marked evolution of gas
  3. concentrationConcentration

Sources & evidence

ORD record
ord-cc37d3126bc34d919b8ebc0bfa65f70f
Source dataset
uspto-grants-2016_06
Patent number
US09375002B2

Reaction notes

Loading…