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

HRID 1936198ノート

反応式

HRID 1936198 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-1a793013bf3144bbb0c0e8a6ff0b4c24
出典データセット
uspto-grants-2002_05
特許番号
US06388131B2

反応ノート

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