Thionyl Chloride → 2-Chloro-4-methyl-1,3-thiazole-5-sulfonyl chloride

HRID 1362778Notes

Reaction equation

HRID 1362778 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.S(Cl)(Cl)=O.[Cl:12][S:13](O)(=[O:15])=[O:14]>>[Cl:1][C:2]1[S:3][C:4]([S:13]([Cl:12])(=[O:15])=[O:14])=[C:5]([CH3:7])[N:6]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 30153282-Chloro-4-methylthiazole

Product 1

HCID 120942502-Chloro-4-methyl-1,3-thiazole-5-sulfonyl chlorideYield 17,947.6%

Procedure

150 g (1.12 mol) of 2-chloro-4-methyl-1,3-thiazole are added dropwise at room temperature to a solution of 331 g (2.81 mmol) of thionyl chloride in 653 g (5.61 mmol) of chlorosulfonic acid. The solution is heated to reflux for 48 h. The mixture is then added to 3 l of ice-water and extracted with 4×400 ml of dichloromethane. The combined organic phases are washed with 2.5 l of water, dried over sodium sulfate and concentrated. Distillation of the crude product results in 233.7 g of product in the form of an oil. (Boiling point 87-96° C., 0.7 mbar, GC 98.1%, yield 89.6%).

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 48 h
  3. extractionextracted with 4×400 ml of dichloromethane
  4. washThe combined organic phases are washed with 2.5 l of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-ef97eaac27a2463196f969ddc43872fa
Source dataset
uspto-grants-2011_02
Patent number
US07883713B2

Reaction notes

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