Sodium Carbonate → HCID 69222745, compound

HRID 2056622Notes

Reaction equation

HRID 2056622 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:21]1[S:22][C:23]2[C:29]([N+:30]([O-:32])=[O:31])=[C:28]([O:33][CH3:34])[CH:27]=[CH:26][C:24]=2[N:25]=1>O.COCCOC>[CH3:34][O:33][C:28]1[CH:27]=[CH:26][C:24]2[N:25]=[C:21]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[S:22][C:23]=2[C:29]=1[N+:30]([O-:32])=[O:31]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 59659339HCID 59659339, compound

Product 1

HCID 69222745HCID 69222745, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85.5 °C

Procedure

0.716 g (4.16 mmol; 1.1 equivalent) of 2-naphthalene 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 1.09 g (3.78 mmol) of 2-bromo-6-methoxy-7-nitro-1,3-benzothiazole and 131 mg (0.114 mmol; 0.03 equivalent) of palladium tetrakis-triphenylphosphine in 30 ml of 1,2-dimethoxyethane. The reaction mixture is maintained under stirring at 85.5° C. for 18 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 saturated aqueous solution of 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). 1.06 g (83% yield) of 6-methoxy-2-(2-naphthyl)-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 saturated aqueous solution of 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-50ca719b5c4b4f668b5dded737a250f2
Source dataset
uspto-grants-2008_02
Patent number
US07335674B2

Reaction notes

Loading…