Water → N-[4-(5-Fluorobenzothiazol-2-ylmethoxy)phenyl]butyramide

HRID 1597792Notes

Reaction equation

HRID 1597792 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH2:9][CH2:10][CH3:11].[F:14][C:15]1[CH:16]=[CH:17][C:18]2[S:22][C:21]([CH2:23][O:24][C:25]3[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=3)=[N:20][C:19]=2[CH:32]=1.O>C(Cl)Cl>[F:14][C:15]1[CH:16]=[CH:17][C:18]2[S:22][C:21]([CH2:23][O:24][C:25]3[CH:31]=[CH:30][C:28]([NH:29][C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:27][CH:26]=3)=[N:20][C:19]=2[CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 189322374-(5-Fluorobenzothiazol-2-ylmethoxy)aniline

Product 1

HCID 18932318N-[4-(5-Fluorobenzothiazol-2-ylmethoxy)phenyl]butyramideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.09 ml of triethylamine and 0.07 ml of butyryl chloride were added to a solution of 150.8 mg of 4-(5-fluorobenzothiazol-2-ylmethoxy)aniline [prepared as described in step (b) above] in 3 ml of methylene chloride cooled in an ice-water bath. The temperature of the resulting mixture was then elevated to room temperature and the mixture was stirred for 1 hour. At the end of this time, water was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. 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 then removed by evaporation under reduced pressure and the resulting residue was recrystallized from a mixed solvent of methylene chloride and hexane to give 104.5 mg (yield 55%) of the title compound as a solid having a melting point of 201° to 202° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas then elevated to room temperature
  3. extractionthe resulting mixture was extracted with methylene chloride
  4. extractionThe resulting extract
  5. washwas washed consecutively with water
  6. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  7. customThe solvent was then removed by evaporation under reduced pressure
  8. customthe resulting residue was recrystallized from a mixed solvent of methylene chloride and hexane

Sources & evidence

ORD record
ord-2c956fa856aa4c6fbf5fcb9c27423468
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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