Acetaminophen → N-[4-(6-Methoxybenzothiazol-2-ylmethoxy)phenyl]acetamide

HRID 1597784Notes

Reaction equation

HRID 1597784 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(=[O:5])[CH3:4].Br[CH2:15][C:16]1[S:17][C:18]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:19]=2[N:20]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:26][O:25][C:23]1[CH:22]=[CH:21][C:19]2[N:20]=[C:16]([CH2:15][O:13][C:10]3[CH:11]=[CH:12][C:7]([NH:6][C:3](=[O:5])[CH3:4])=[CH:8][CH:9]=3)[S:17][C:18]=2[CH:24]=1

Participants

6

Reactant 4

HCID 1983AcetaminophenHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 107063232-Bromomethyl-6-methoxybenzothiazole

Product 1

HCID 18932235N-[4-(6-Methoxybenzothiazol-2-ylmethoxy)phenyl]acetamideYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

57.6 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 197.8 mg of 4-acetamidophenol in 4 ml of dimethylformamide cooled in an ice-water bath and the resulting mixture was stirred at this temperature for 5 minutes. A solution of 371.5 mg of 2-bromomethyl-6-methoxybenzothiazole [prepared as described in step (a) above] in 1 ml of dimethylformamide was added to the reaction mixture, the temperature of the mixture was elevated to room temperature and the mixture was stirred for 2 hours. At the end of this time, a saturated aqueous ammonium chloride solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The resulting extract was washed consecutively with water and an aqueous sodium chloride solution and them dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of hexane and ethyl acetate to give 399.1 mg (yield 93%) of the title compound as a solid having a melting point of 145°-147° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas elevated to room temperature
  3. stirringthe mixture was stirred for 2 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. extractionThe resulting extract
  6. washwas washed consecutively with water
  7. dry with materialan aqueous sodium chloride solution and them dried over anhydrous sodium sulfate
  8. customThe solvent was then removed by evaporation under reduced pressure
  9. customthe resulting residue was purified by column chromatography through silica gel using a 1:2
  10. additionby volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-4c8e1121d9604b9b995810a2db201ffd
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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