Benzenesulfonyl chloride → N-Benzenesulfonyl-N-(4-bromo-3-tert-butyl-5-isoxazolyl) benzenesulfonamide

HRID 842883ノート

反応式

HRID 842883 の反応式
[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]=1[Br:11].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:12]1([S:18]([N:1]([C:2]2[O:6][N:5]=[C:4]([C:7]([CH3:8])([CH3:10])[CH3:9])[C:3]=2[Br:11])[S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 2

HCID 7369Benzenesulfonyl chlorideHCID 186173124-Bromo-3-(tert-butyl)isoxazol-5-amine

生成物 1

HCID 18617308N-Benzenesulfonyl-N-(4-bromo-3-tert-butyl-5-isoxazolyl) benzenesulfonamide収率 60.1%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

5-Amino-4-bromo-3-tert-butylisoxazole (440 mg, 2.0 mmol) was dissolved in dry pyridine (2 ml). Benzenesulfonyl chloride (344 mg, 2.0 mmol) and 4-dimethylamino-pyridine (5 mg) was added and the reaction was stirred at 50° C. for 16 h. The reaction mixture was diluted with ethyl acetate (20 ml), washed with 1N HCl (2×10 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was recrystallized from ethyl acetate/hexanes to give 300 mg (60% yield) of N-benzenesulfonyl-N-(4-bromo-3-tert-butyl-5-isoxazolyl)benzenesulfonamide.

後処理

  1. washwashed with 1N HCl (2×10 ml)
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customto yield a crude product, which
  5. customwas recrystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-0cfcf7686fab4d6287160eee6661b9d6
出典データセット
uspto-grants-2002_04
特許番号
US06376523B1

反応ノート

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