2-Aminopyrimidine → 2-Aminopyrimidine-5-sulfonyl chloride

HRID 1173092Notes

Reaction equation

HRID 1173092 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[NH2:6][C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1.S(Cl)(Cl)=O>O>[NH2:6][C:7]1[N:12]=[CH:11][C:10]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 79782-AminopyrimidineHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acid

Product 1

HCID 158856182-Aminopyrimidine-5-sulfonyl chlorideYield 27.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

21 ml (0.316 mol) of chlorosulfonic acid was cooled in ice-water and 3 g (0.032 mol) of 2-aminopyrimidine was added thereto little by little under stirring. 9.2 ml (0.126 mol) of thionyl chloride was further added thereto, followed by stirring at 150° C. for 70 hours. The reaction solution was returned to room temperature, poured into water and extracted with ethyl acetate. The extract was dried over sodium sulfate and then concentrated to dryness, to give 1.7 g of the title compound.

Workup

  1. stirringby stirring at 150° C. for 70 hours
  2. customwas returned to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5bd5c13933cd44ffaa27349f048a26b7
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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