Saccharin → 1,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one

HRID 1252689Notes

Reaction equation

HRID 1252689 reaction equation
[H-].[Na+].[S:3]1([C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7](=[O:8])[NH:6]1)(=[O:5])=[O:4].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19]Br>CN(C)C=O>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][N:6]1[C:7](=[O:8])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[S:3]1(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 5143SaccharinHCID 80561,4-DibromobutaneHCID 24758Sodium hydride

Product 1

HCID 107817741,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-oneYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 60% sodium hydride in mineral oil (1.1 g) was added to dry dimethylformamide (50 ml) at room temperature while stirring. Saccharin (5 g) was gradually added to the suspension at room temperature, followed by stirring for 30 minutes. To the resultant mixture, 1,4-dibromobutane (29.5 g) was dropwise added, and the mixture was kept at an inner temperature of 90° to 100° C. for 5 hours. After completion of the reaction, insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using chloroform as an eluent to give the objective compound (7.98 g). IR νmaxfilm (cm-1): 1730, 1595, 1460, 1440, 1330.

Workup

  1. stirringby stirring for 30 minutes
  2. customAfter completion of the reaction, insoluble materials
  3. customwere removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7dd8160f503b42d5aa4d878123407854
Source dataset
uspto-grants-1988_05
Patent number
US04745117

Reaction notes

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