2-Fluoro-5-nitrobenzene-1-sulfonamide → 5-amino-2-fluorobenzenesulfonamide

HRID 1725669노트

반응식

HRID 1725669 반응식
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][C:10]=1[F:11])(=[O:4])=[O:3]>ClCCl.CO.[Pd]>[NH2:12][C:7]1[CH:8]=[CH:9][C:10]([F:11])=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:6]=1

참가 물질

5

반응물 1

HCID 77303242-Fluoro-5-nitrobenzene-1-sulfonamide

생성물 1

HCID 432553875-amino-2-fluorobenzenesulfonamide수율 77.9%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-aminosulfonyl-4-fluoronitrobenzene (360 mg, 1.62 mmol) in dichloromethane (6 mL) and methanol (3 mL) was added 10% Pd/C (36 mg) and shaken under a hydrogen atmosphere at 50 psi for 15 minutes. The mixture was filtered through Celite and the cake was washed with methanol (5 mL). The combined organic solvent was concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 240 mg of 5-amino-2-fluorobenzensulfonamide as a light yellow solid. 1H NMR (DMSO-d6): δ 7.38 (s, 2H), 7.03-6.94 (m, 2H), 6.70-6.66 (m, 1H), 5.33 (s, 1H).

후처리

  1. filtrationThe mixture was filtered through Celite
  2. washthe cake was washed with methanol (5 mL)
  3. concentrationThe combined organic solvent was concentrated under reduced pressure
  4. customto give crude product, which
  5. customwas further purified by flash column chromatography (ethyl acetate:hexanes 1:1)

출처 및 근거

ORD 기록
ord-4079e3ad79bc40f9a1c582da291d9c62
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491732B2

반응 노트

불러오는 중…