4-Nitrophenol → O-(5-Fluorobenzothiazol-2-ylmethyl)-4-nitrophenol

HRID 1597790Notes

Reaction equation

HRID 1597790 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:18]=2[N:19]=1.[Cl-].[NH4+]>CN(C)C=O>[F:24][C:21]1[CH:22]=[CH:23][C:17]2[S:16][C:15]([CH2:14][O:12][C:9]3[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=3)=[N:19][C:18]=2[CH:20]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 144586272-(Bromomethyl)-5-fluorobenzo[d]thiazole

Product 1

HCID 70124450O-(5-Fluorobenzothiazol-2-ylmethyl)-4-nitrophenolYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

452.9 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 1.5 g of 4-nitrophenol in 30 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at this temperature for 5 minutes, after which a solution of 2.79 g of 2-bromomethyl-5-fluorobenzothiazole in 5 ml of dimethylformamide was added thereto. The temperature of the resulting mixture was elevated to room temperature and the mixture was then 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 a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was washed with a mixed solvent of methylene chloride and hexane to give 2.33 g of the title compound as a crude crystalline solid.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas elevated to room temperature
  3. stirringthe mixture was then 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 materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation under reduced pressure
  9. washthe resulting residue was washed with a mixed solvent of methylene chloride and hexane

Sources & evidence

ORD record
ord-d45fd4ca75924c92ae5cae17ae231592
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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