Water → 2-Fluoro-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)aniline

HRID 1512994ノート

反応式

HRID 1512994 の反応式
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C(N(CC)CC)C.[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][C:21]=1[N+:30]([O-])=O.O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:1]2[C:2]3[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=3[CH2:4][CH2:5][CH2:6][CH2:7]2)(=[O:28])=[O:27])=[CH:22][C:21]=1[NH2:30]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineHCID 27827994-Fluoro-3-nitrobenzene-1-sulfonyl chloride

生成物 1

HCID 593099752-Fluoro-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)aniline収率 38.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2,3,4,5-tetrahydro-1H-benzo[B]azepine (0.37 g), triethylamine (0.35 mL) and 4-dimethylaminopyridine (26 mg) in methylene chloride (8 mL) was added 4-fluoro-3-nitrobenzenesulfonyl chloride (0.5 g), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in tetrahydrofuran (7 mL). To the solution were added methanol (7 mL) and nickel(II) bromide (23 mg). To the mixture was added sodium borohydride (0.24 g) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes, and then stirred at room temperature for 30 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1) to give the title compound (0.26 g).

後処理

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with 1 mol/L hydrochloric acid, water and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue was dissolved in tetrahydrofuran (7 mL)
  6. additionTo the solution were added methanol (7 mL) and nickel(II) bromide (23 mg)
  7. additionTo the mixture was added sodium borohydride (0.24 g) under ice-
  8. temperaturecooling
  9. stirringthe mixture was stirred at the same temperature for 30 minutes
  10. stirringstirred at room temperature for 30 minutes
  11. additionTo the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution
  12. extractionthe resulting mixture was extracted with ethyl acetate
  13. washThe extract was washed with water and brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customThe solvent was removed under reduced pressure
  16. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-1234f3f6498a447f82ae204adc80b38d
出典データセット
uspto-grants-2012_07
特許番号
US08217069B2

反応ノート

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