1,4-Dichlorobutane → 2-(4-Chloro-1-butyl)-3(2H)-benz[d]isothiazolone 1,1-Dioxide

HRID 2296024Notes

Reaction equation

HRID 2296024 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[Na].[Cl:14][CH2:15][CH2:16][CH2:17][CH2:18]Cl>CN(C)C=O>[Cl:14][CH2:15][CH2:16][CH2:17][CH2:18][N:4]1[C:5](=[O:6])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[S:1]1(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 80591,4-DichlorobutaneHCID 24181110Benzosulfinide sodium; Garantose sodium

Product 1

HCID 132898002-(4-Chloro-1-butyl)-3(2H)-benz[d]isothiazolone 1,1-DioxideYield 12.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium saccharin (5.6 g, 0.027 mole) and 1,4-dichlorobutane (14.9 ml, 0.135 mole) were taken into 100 ml of dimethylformamide and heated on a steam bath for 4 hours. The reaction mixture was evaporated in vacuo to an oil and the oil extracted with 100 ml of hexane. Residual hexane was removed from the remaining oil by vacuum evaporation to yield the title product (956 mg).

Workup

  1. temperatureheated on a steam bath for 4 hours
  2. customThe reaction mixture was evaporated in vacuo to an oil
  3. extractionthe oil extracted with 100 ml of hexane
  4. customResidual hexane was removed from the remaining oil by vacuum evaporation

Sources & evidence

ORD record
ord-f2bad0d19dde4740afd65929e8dfee3d
Source dataset
uspto-grants-1984_01
Patent number
US04427679

Reaction notes

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