Sodium hydride → N-[4-(6-Fluorobenzothiazol-2-ylmethoxy)phenyl]acetamide

HRID 1597782Notes

Reaction equation

HRID 1597782 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:18]=[CH:17][C:7]2[N:8]=[C:9]([CH2:11][O:12]S(C)(=O)=O)[S:10][C:6]=2[CH:5]=1.[Cl-].[NH4+:20]>CN(C)C=O>[F:3][C:4]1[CH:18]=[CH:17][C:7]2[N:8]=[C:9]([CH2:11][O:12][C:4]3[CH:18]=[CH:17][C:7]([NH:20][C:11](=[O:12])[CH3:9])=[CH:6][CH:5]=3)[S:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 189321066-Fluoro-2-methanesulfonyloxymethylbenzothiazole

Product 1

HCID 18932502N-[4-(6-Fluorobenzothiazol-2-ylmethoxy)phenyl]acetamideYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

18.8 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 64.6 mg of4-acetamidophenol in 1.3 ml of dimethylformamide cooled in an ice-water bath, and the resulting mixture stirred at the same temperature for 3 minutes. A solution of 122.8 mg of 6-fluoro-2-methanesulfonyloxymethylbenzothiazole [prepared as described in step (c) above] in 0.4 ml of dimethylformamide was then added to the reaction mixture. The temperature of the resulting mixture was then elevated to room temperature and the mixture was stirred for 3 hours. At the end of this time, a saturated aqueous ammonium chloride solution was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed consecutively with water and an aqueous sodium chloride solution and then dried over sodium sulfate. The solvent was 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 as the eluent, to give 38.3 mg (yield 28%) of the title compound as a solid having a melting point of 204° to 205° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas then elevated to room temperature
  3. stirringthe mixture was stirred for 3 hours
  4. extractionthe resulting 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 then dried over sodium sulfate
  8. customThe solvent was 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 as the eluent

Sources & evidence

ORD record
ord-8b530076007f4fdf86f8248b17acb2b8
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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