Benzisothiazole → 3-Chloro-1,2-benzisothiazole

HRID 341975

Reaction equation

HRID 341975 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[N:2]1.S(Cl)([Cl:13])(=O)=O>ClC1C=CC=CC=1>[Cl:13][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][N:2]=1

Participants

4

Reactant 2

HCID 9225BenzisothiazoleHCID 24648Sulfuryl chloride

Product 1

HCID 5981903-Chloro-1,2-benzisothiazoleYield 96%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In a 300 ml four-necked flask equipped with a stirrer, a thermometer, and a condenser, 100 g of monochlorobenzene was placed in advance, to which 27.0 g (0.2 mol) of 1,2-benzisothiazole was added under nitrogen atmosphere. 32.4 g (0.22 mol) Of sulfuryl chloride was added dropwise thereto while stirring at a temperature of from 70° to 80° C. and allowed to react for 1 hour at the same temperature. After the termination of the reaction, the reaction mixture was subjected to distilling off of the solvent and then to distillation under reduced pressure to give 32.5 g of 3-chloro-1,2-benzisothiazole (boiling point: 116° to 118° C./5 mm Hg, melting point: 38° to 40° C.). The yield was 96% to the 1,2-benzisothiazole.

Workup

  1. customIn a 300 ml four-necked flask equipped with a stirrer
  2. additionwas added under nitrogen atmosphere
  3. customto react for 1 hour at the same temperature
  4. customAfter the termination of the reaction
  5. distillationto distilling off of the solvent
  6. distillationto distillation under reduced pressure

Sources & evidence

ORD record
ord-c4037742b9154d1288c92c8b72230c83
Source dataset
uspto-grants-1999_01
Patent number
US05856504

Linked notes

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