Dimethylformamide → HCID 18932175, compound

HRID 1597818Notes

Reaction equation

HRID 1597818 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9](C)[CH:8]=1)(=[O:5])[CH3:4].Br[CH2:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.[Cl-].[NH4+].[CH3:28]N(C)C=O>>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[CH2:16][O:13][C:10]1[CH:9]=[CH:8][C:7]([NH:6][C:3](=[O:5])[CH3:4])=[C:12]([CH3:28])[CH:11]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 85384Acetamide, N-(4-hydroxy-3-methylphenyl)-HCID 27762582-(Bromomethyl)-1,3-benzothiazole

Product 1

HCID 18932175HCID 18932175, compoundYield 82%

Procedure

23.3 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 97.7 mg of 4-acetamido-2-methylphenol in 3 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 3 minutes, and then 132.2 mg of 2-bromomethylbenzothiazole [prepared as described in step (a) above] were added. The temperature of the resulting mixture was 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 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 recrystallised from a mixed solvent of methylene chloride and hexane to give 85.7 mg (yield 82%) of the title compound as a solid having a melting point of 179° to 182° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customwas 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 materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  8. customThe solvent was then removed by evaporation under reduced pressure
  9. customthe resulting residue was recrystallised from a mixed solvent of methylene chloride and hexane

Sources & evidence

ORD record
ord-caa2b10b1fb4470aa02952c30421add2
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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