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

HRID 1597790ノート

反応式

HRID 1597790 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d45fd4ca75924c92ae5cae17ae231592
出典データセット
uspto-grants-1998_04
特許番号
US05736487

反応ノート

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