1-Bromo-3-chloropropane → N-(3-Chloropropyl)-5,6-dimethoxy-1,2-benzisothiazoline-1,1-dioxide

HRID 259535Notes

Reaction equation

HRID 259535 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:14][CH3:15])=[CH:5][C:6]2[S:10](=[O:12])(=[O:11])[N:9]=[CH:8][C:7]=2[CH:13]=1.Br[CH2:17][CH2:18][CH2:19][Cl:20]>[OH-].[Na+].C(O)C>[Cl:20][CH2:19][CH2:18][CH2:17][N:9]1[CH2:8][C:7]2[CH:13]=[C:3]([O:2][CH3:1])[C:4]([O:14][CH3:15])=[CH:5][C:6]=2[S:10]1(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 681175355,6-Dimethoxy-1,2-benzisothiazoline-1,1-dioxide

Product 1

HCID 53817430N-(3-Chloropropyl)-5,6-dimethoxy-1,2-benzisothiazoline-1,1-dioxide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.4 gm (10.5 millimols) of the compound obtained in step (d) were dissolved in a mixture of 15 ml of an aqueous 2.5% sodium hydroxide solution and 30 ml of ethanol, and the solution was refluxed for 8 hours after addition of 10 ml of 3-bromo-1-chloro-propane. The reaction mixture was thereafter evaporated to half its volume, diluted with water and extracted with chloroform. After drying of the organic phase it was evaporated in vacuo, and the desired product was obtained as a highly viscous oil. Rf -value (chloroform/methanol = 19/1: 0.8.

Workup

  1. temperaturethe solution was refluxed for 8 hours
  2. customThe reaction mixture was thereafter evaporated to half its volume
  3. additiondiluted with water
  4. extractionextracted with chloroform
  5. customAfter drying of the organic phase it
  6. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-eaa1d893d50349c2b4e40f9b270b2a2a
Source dataset
uspto-grants-1977_07
Patent number
US04038407

Reaction notes

Loading…