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

HRID 378454노트

반응식

HRID 378454 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b52eb83c2bb54708b311f2c8b2da0b02
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06030991

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