Hydroquinone → Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-butoxymethylcarbamate

HRID 1597805Notes

Reaction equation

HRID 1597805 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:23][OH:24])[C:19](=[O:22])[O:20][CH3:21])=[C:14]([CH3:25])[CH:13]=1.S(=O)(=O)(O)O.[C:31]1([CH:38]=CC(O)=[CH:34][CH:33]=1)O>C(O)CCC.S([O-])(O)(=O)=O.[Na+]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:23][O:24][CH2:38][CH2:31][CH2:33][CH3:34])[C:19](=[O:22])[O:20][CH3:21])=[C:14]([CH3:25])[CH:13]=1

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 18932060Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-hydroxymethylcarbamate

Product 1

HCID 18932300Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-butoxymethylcarbamateYield 9,330.4%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 516919Sodium BisulfateSolvent

Conditions

Temperature
85 °C

Procedure

49.8 mg of methyl N-hydroxymethyl-N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate [prepared as described in Example 19] were dissolved in 2 ml of butanol at room temperature, and the pH of the resulting solution was adjusted with concentrated sulfuric acid to pH 3. A catalytic amount of hydroquinone (2 mg) was added to the resulting mixture at room temperature and the mixture was then stirred for 1 hour at 85° C. The reaction mixture was then cooled to room temperature, diluted with aqueous sodium hydrogen sulfate and then extracted with ethyl acetate. The resulting extract was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give a residue which was purified by column chromatography through silica gel using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 702.5 mg (yield 94.1%) of the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. extractionThe resulting extract
  4. washwas washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation under reduced pressure
  7. customto give a residue which
  8. customwas purified by column chromatography through silica gel using a 2:1
  9. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-324d1eeed9474786aa5c352207e01f29
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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