Water → 1,2-Benzisothiazol-5-amine, 3-chloro-

HRID 277384Notes

Reaction equation

HRID 277384 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.O>C1(C)C=CC=CC=1.Cl.[Fe]>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]2[S:4][N:3]=[C:2]([Cl:1])[C:6]=2[CH:7]=1

Participants

6

Reactant 2

HCID 962WaterHCID 1980981,2-Benzisothiazole, 3-chloro-5-nitro-

Product 1

HCID 1987661,2-Benzisothiazol-5-amine, 3-chloro-

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3-chloro-5-nitro-1,2-benzisothiazole (2.00 g) in toluene is treated with iron powder (8.40 g, 325 mesh) and concentrated hydrochloric acid (8 drops), heated to reflux, treated dropwise with water (8.00 mL), refluxed for 35 minutes, cooled to room temperature, and filtered through diatomaceous earth. The resultant filtrate is concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and an ethyl acetate/hexanes solution (1:1) gives the title product.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturerefluxed for 35 minutes
  4. filtrationfiltered through diatomaceous earth
  5. concentrationThe resultant filtrate is concentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-a5e1958171924e208d77241b945705c9
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

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