1-Bromo-3-chloropropane → 2-(3-Chloroprop-1-yl)-3,3-dimethyl-2,3-dihydro-1,2-benzoisothia-zole 1,1-dioxide

HRID 1699444Notes

Reaction equation

HRID 1699444 reaction equation
[CH3:1][C:2]1([CH3:13])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:12])(=[O:11])[NH:3]1.CC(C)([O-])C.[K+].Br[CH2:21][CH2:22][CH2:23][Cl:24]>CN(C=O)C>[Cl:24][CH2:23][CH2:22][CH2:21][N:3]1[C:2]([CH3:13])([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4]1(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 44473552,3-Dihydro-3,3-dimethyl-1,2-benzisothiazole 1,1-dioxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 701623242-(3-Chloroprop-1-yl)-3,3-dimethyl-2,3-dihydro-1,2-benzoisothia-zole 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5.9 g (3 mmol) of 3,3-dimethyl-2,3-dihydro-1,2-benzoisothiazole 1,1-dioxide in 150 ml of DMF at room temperature was, after addition of 3.7 g (3.3 mmol) of potassium t-butoxide, heated under nitrogen to 80° C. Then 14.2 g (9 mmol) of 1-bromo-3-chloropropane were rapidly added and the mixture was stirred at 100° C. for 30 min. Pouring into ice-water was followed by extraction with ether, and the organic phases were washed with water, dried with sodium sulfate and then evaporated so that the product resulted as crystals which could be filtered off with suction. 6.7 g (82%) of substance were obtained. Melting point 107° C.

Workup

  1. customat room temperature
  2. extractionwas followed by extraction with ether
  3. washthe organic phases were washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated so that the product
  6. customresulted as crystals which
  7. filtrationcould be filtered off with suction
  8. custom6.7 g (82%) of substance were obtained

Sources & evidence

ORD record
ord-51095bef9663450c8d7d2a4bbd812848
Source dataset
uspto-grants-2002_02
Patent number
US06346622B1

Reaction notes

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