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

HRID 558507Notes

Reaction equation

HRID 558507 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 43%

Conditions

Temperature
120 °C

Procedure

2-Chloro-4-methyl-thiazole (33 g, 180 mmol) was added dropwise to a solution of thionyl chloride (32.7 mL, 451 mmol) and chlorosulfonic acid (60.2 mL, 902 mmol). The reaction mixture was stirred for 48 h at 120° C., cooled then poured onto ice-water and extracted 3 times with CH2Cl2, dried over Na2SO4, filtered, and concentrated to give a crude liquid. The product was isolated by simple distillation (17 mbar at 85-95° C.) to give 2-Chloro-4-methyl-thiazole-5-sulfonyl chloride (17.85 g, 43%) as a light-yellow liquid. MS (ISP) 233.0 [(M+H)+].

Workup

  1. temperaturecooled
  2. additionthen poured onto ice-water
  3. extractionextracted 3 times with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude liquid
  8. customThe product was isolated by simple distillation (17 mbar at 85-95° C.)

Sources & evidence

ORD record
ord-e8526f73f06743d0bccd14218128b9db
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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