P-Anisidine → 4-Fluoro-1-[(4-methoxyphenyl)aminosulfonyl]-3-nitrobenzene

HRID 1936198노트

반응식

HRID 1936198 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>CO>[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]

참가 물질

4

반응물 2

HCID 7732P-AnisidineHCID 27827994-Fluoro-3-nitrobenzene-1-sulfonyl chloride

생성물 1

HCID 155506334-Fluoro-1-[(4-methoxyphenyl)aminosulfonyl]-3-nitrobenzene수율 60%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

p-Anisidine (760 mg, 6.18 mmol) was added to a solution of 4-fluoro-3-nitrophenylsulfonyl chloride (740 mg, 3.09 mmol; Example A) in MeOH (10 ml) at ambient temperature. After stining at room temperature for 15 min, the reaction mixture was concentrated under reduced pressure and the residue was taken up in ethyl acetate and filtered through a pad of silica gel. Concentration of the filtrate, followed by chromatography, provided 603 mg (60% yield) of the title compound. 1H-NMR (CDCl3): δ 8.42 (1H, dd, J=2.3, 6.8 Hz), 7.88 (1H, ddd, J=2.4, 4.0, 8.8 Hz), 7.33 (1H, dd, J=8.8, 9.9 Hz), 6.98 (2H, m), 6.81 (2H, m), 6.45 (1H, s), 3.77 (3H, s). MS (EI): 326 (11, M+), 122 (100). Anal. Calcd. for C13H11FN2O5S: C, 47.85; H, 3.40; N, 8.59; S, 9.83. Found: C, 47.68; H, 3.44; N, 8.54; S, 9.88.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltered through a pad of silica gel

출처 및 근거

ORD 기록
ord-1a793013bf3144bbb0c0e8a6ff0b4c24
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06388131B2

반응 노트

불러오는 중…