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

HRID 617688Notes

Reaction equation

HRID 617688 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.[NH:13]1[CH2:18][CH2:17]O[CH2:15][CH2:14]1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:14]([N:13]([CH2:18][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)[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8083MorpholineHCID 64783Pseudosaccharin chloride

Product 1

HCID 2279901,2-benzisothiazol-3-amine, n,n-diethyl-, 1,1-dioxideYield 91.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

10.0 g of pseudosaccharine chloride are initially introduced in 150 ml of toluene. 4.4 g of morpholine diluted with 25 ml of toluene are added dropwise at room temperature over the course of 30 minutes. Since the reaction is exothermic, the mixture is cooled with an ice bath. After a further 30 minues, 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 10.8 g (86%) of 3-diethylaminobenzoisothiazole 1,1-dioxide.

Workup

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

Sources & evidence

ORD record
ord-e0ffcf7317074a389f0b4d72fb0ff44e
Source dataset
uspto-grants-1999_09
Patent number
US05952282

Reaction notes

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