Sodium Carbonate → HCID 67392848, compound

HRID 908668Notes

Reaction equation

HRID 908668 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](B(O)O)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:20]1[S:21][C:22]2[C:28]([N+:29]([O-:31])=[O:30])=[C:27]([O:32][CH3:33])[CH:26]=[CH:25][C:23]=2[N:24]=1>O.COCCOC>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:20]3[S:21][C:22]4[C:28]([N+:29]([O-:31])=[O:30])=[C:27]([O:32][CH3:33])[CH:26]=[CH:25][C:23]=4[N:24]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 59659339HCID 59659339, compound

Product 1

HCID 67392848HCID 67392848, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

0.697 g (4.2 mmol; 1.1 equivalent) of 1,3-benzodioxol-5-yl boronic acid as well as a solution of 1.2 g (11.35 mmol; 3 equivalents) of sodium carbonate in 15 ml of water are added to a suspension of 1.1 g (3.82 mmol) of 2-bromo-6-methoxy-7-nitro-1,3-benzothiazole and 133 mg (0.115 mmol; 0.03 equivalent) of palladium tetrakis-triphenylphosphine in 30 ml of 1,2-dimethoxyethane. The reaction mixture is maintained under stirring at 90° C. for 4 hours, then after concentration under reduced pressure, 100 ml of ethyl acetate is added to the medium which is then washed with twice 75 ml of a solution of water saturated with sodium chloride. The organic phase is dried over sodium sulphate then the solvents are evaporated off under reduced pressure and the residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane mixture 1:2). 0.960 g (yield of 76%) of 2-(1,3-benzodioxol-5-yl)-6-methoxy-7-nitro-1,3-benzothiazole is obtained in the form of beige powder.

Workup

  1. temperatureThe reaction mixture is maintained
  2. concentrationafter concentration under reduced pressure, 100 ml of ethyl acetate
  3. additionis added to the medium which
  4. washis then washed with twice 75 ml of a solution of water saturated with sodium chloride
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customthe solvents are evaporated off under reduced pressure
  7. customthe residue is purified by chromatography on a silica column (eluent: ethyl acetate/heptane mixture 1:2)

Sources & evidence

ORD record
ord-46daa666300747d6b6806ea303055c7f
Source dataset
uspto-grants-2011_09
Patent number
US08017637B2

Reaction notes

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