Allyl bromide → 7-Allyloxy-1,2-benzisothiazole

HRID 2399698Notes

Reaction equation

HRID 2399698 reaction equation
[OH:1][C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15].[OH-].[K+]>C1COCC1.O>[CH2:15]([O:1][C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH:14]=[CH2:13]

Participants

7

Reactant 4

HCID 7841Allyl bromide2×HCID 14797Potassium HydroxideHCID 24758Sodium hydride2×HCID 19384356Benzo[d]isothiazol-7-ol

Product 1

HCID 193843547-Allyloxy-1,2-benzisothiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of 7-hydroxy-1,2-benzisothiazole are dissolved in 20 ml of THF, and 460 mg of sodium hydride (60%) are added to the mixture at 0° C. When the evolution of gas has ended, 1 ml of allyl bromide is added dropwise, the reaction mixture is stirred for one day at room temperature. Again, 1 ml of allyl bromide and 40 mg of sodium hydride are added, and the mixture is stirred for 2 days under reflux. The reaction mixture is poured into water, rendered basic using 1 N potassium hydroxide solution and extracted using ethyl acetate. The organic phase is washed with saline, dried over sodium sulfate, filtered and concentrated. Silica gel chromatography with ethyl acetate/hexane (1:5) as mobile phase gives 2.0 g of 7-allyloxy-1,2-benzisothiazole; nD20 =1.6039 .

Workup

  1. stirringthe mixture is stirred for 2 days
  2. temperatureunder reflux
  3. extractionextracted
  4. washThe organic phase is washed with saline
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ef48314bc9a549dfb2a0cd91337951a6
Source dataset
uspto-grants-1995_09
Patent number
US05451595

Reaction notes

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