2,4-Dimethylphenol → 2-(2,4-Dimethylphenoxy)-7-nitro-1,3-benzothiazole

HRID 2235503Notes

Reaction equation

HRID 2235503 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[OH:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[O:22][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 77712,4-DimethylphenolHCID 11430Potassium CarbonateHCID 685819982-Bromo-7-nitrobenzo[d]thiazole

Product 1

HCID 685813382-(2,4-Dimethylphenoxy)-7-nitro-1,3-benzothiazoleYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-7-nitro-1,3-benzothiazole (200 mg, 0.772 mmol), 2,4-dimethylphenol (0.093 ml, 0.772 mmol) and potassium carbonate (128 mg, 0.772 mmol) in DMF (10 ml) was stirred at 80° C. for 15 h. The mixture was diluted with water and extracted with ethyl acetate (AcOEt). The extract was washed with saturated NaHCO3 solution and brine, dried over Magnesium sulfate and concentrated under vacuum. The residue was purified by chromatography eluting with 10% AcOEt in n-hexane to afford 226 mg of the title compound.

Workup

  1. extractionextracted with ethyl acetate (AcOEt)
  2. washThe extract was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography
  6. washeluting with 10% AcOEt in n-hexane

Sources & evidence

ORD record
ord-2081665b69384beb8aa6bd5814147679
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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