Pyridine → 1,2-benzisothiazol-3-amine, n,n-diethyl-, 1,1-dioxide

HRID 617687Notes

Reaction equation

HRID 617687 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7](Cl)=[N:8][S:9](=[O:11])(=[O:10])[C:4]2=[CH:3][CH:2]=1.[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:13]([N:15]([CH2:16][CH3:17])[C:7]1[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[S:9](=[O:11])(=[O:10])[N:8]=1)[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8021DiethylamineHCID 64783Pseudosaccharin chloride

Product 1

HCID 2279901,2-benzisothiazol-3-amine, n,n-diethyl-, 1,1-dioxideYield 85.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

10.0 g of pseudosaccharine chloride are initially introduced in 150 ml of toluene. 3.7 g of diethylamine diluted with 25 ml of toluene are added dropwise at room temperature over the course of 30 minutes. After a further 30 minutes, 50 ml of pyridine in 25 ml of toluene are added and the mixture is subsequently stirred at room temperature for 2.5 hours. The solvent is then removed in vacuo and the residue is stirred up with 350 ml of water. The colorless precipitate is filtered off to give 10.1 g (84%) of 3-diethylaminobenzoisothiazole 1,1-dioxide.

Workup

  1. additionare added dropwise at room temperature over the course of 30 minutes
  2. customThe solvent is then removed in vacuo
  3. stirringthe residue is stirred up with 350 ml of water
  4. filtrationThe colorless precipitate is filtered off

Sources & evidence

ORD record
ord-763dd2f3740548f380376dd919355872
Source dataset
uspto-grants-1999_09
Patent number
US05952282

Reaction notes

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