Thionyl Chloride → 4-Chloromethyl-5-chloro-3-methylisothiazole

HRID 1292814Notes

Reaction equation

HRID 1292814 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[S:10][N:9]=[C:8]([CH3:11])[C:7]=1[CH2:12]O>C(Cl)(Cl)Cl>[Cl:3][CH2:12][C:7]1[C:8]([CH3:11])=[N:9][S:10][C:6]=1[Cl:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 17862899(5-Chloro-3-methyl-isothiazol-4-yl)-methanol

Product 1

HCID 178629054-Chloromethyl-5-chloro-3-methylisothiazoleYield 100.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.26 g (27.44 mmoles) of thionyl chloride was added, at room temperature, to a solution of 1.50 g (9.15 mmoles) of (5-chloro-3-methyl-isothiazol-4-yl)-methanol dissolved in 10 ml of chloroform. The mixture was stirred for 3 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was subjected to vacuum distillation to remove the solvent contained therein, to obtain 1.67 g (yield: quantitative) of 4-chloromethyl-5-chloro-3-methylisothiazole.

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter confirmation of the completion of the reaction
  4. distillationthe reaction mixture was subjected to vacuum distillation
  5. customto remove the solvent

Sources & evidence

ORD record
ord-212906cff606499184c2aabe3d783814
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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