Allyl iodide → 5-Chloro-3-(2-propen-1-yl)-1,3-benzothiazol-2(3H)-one

HRID 657051Notes

Reaction equation

HRID 657051 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH:19]=[CH2:20]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:20][CH:19]=[CH2:18])[C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 6038292(3H)-Benzothiazolone, 5-chloro-

Product 1

HCID 688168665-Chloro-3-(2-propen-1-yl)-1,3-benzothiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Chloro-1,3-benzothiazol-2(3H)-one (1.85 g, 10 mmol) was dissolved in DMF (50 ml) and treated with potassium carbonate (1.66 g, 12 mmol) and allyl iodide (1.1 ml, 12 mmol) then heated at 100° C. for 18 hrs. The solvent was then removed in-vacuo and the residue partitioned between water (100 ml) and ethyl acetate (2×100 ml). The organic layer was washed with saturated brine, separated and dried. Chromatography on silica gel eluting with a gradient of 10-50% ethyl acetate/40-60 petroleum ether gave the title compound as an oil that crystalised on standing (2.14 g, 95%).

Workup

  1. customThe solvent was then removed in-vacuo
  2. customthe residue partitioned between water (100 ml) and ethyl acetate (2×100 ml)
  3. washThe organic layer was washed with saturated brine
  4. customseparated
  5. customdried

Sources & evidence

ORD record
ord-a80f7e8c957547a1bf527268be6bb86e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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