N-Acetylsulfanilyl chloride → Methyl 2-{[2-({[4-(acetylamino)phenyl]sulfonyl}amino)phenyl]thio}benzoate

HRID 746741

反応式

HRID 746741 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].[C:19]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)(=[O:21])[CH3:20]>N1C=CC=CC=1.C(OCC)(=O)C>[C:19]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])(=[O:31])=[O:30])=[CH:27][CH:28]=1)(=[O:21])[CH3:20]

参加物

5

反応物 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 614949Methyl 2-[(2-aminophenyl)sulfanyl]benzoate

生成物 1

HCID 11442458Methyl 2-{[2-({[4-(acetylamino)phenyl]sulfonyl}amino)phenyl]thio}benzoate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of methyl 2-[(2-aminophenyl)thio]benzoate (0.444 g, 1.71 mmol) and 4-(acetylamino)benzenesulfonyl chloride (0.440 g, 1.88 mmol) in pyridine (1.6 mL) was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate and washed with 0.5 N HCl (×2), water (×2), half brine and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography eluted with 1-5% MeOH in DCM to provide the title compound. MS (ES, M+H+): 457.2. 1H NMR (400 MHz, CD3OD) δ 7.92 (bd, J=8 Hz, 1H), 7.75 (bd, J=8 Hz, 1H), 7.55 (bd, J=9.2 Hz, 2H), 7.50-7.44 (m, 3H), 7.42 (bd, J=8 Hz, 1H), 7.18 (bt, J=7.6 Hz, 1H), 7.14 (bt, J=7.6 Hz, 1H), 7.05 (bt, J=8 Hz, 1H), 6.23 (bd, J=8 Hz, 1H), 3.95 (s, 3H), 2.14 (s, 3).

後処理

  1. washwashed with 0.5 N HCl (×2), water (×2), half brine and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 1-5% MeOH in DCM

出典と根拠

ORDレコード
ord-02c64c4ec5bc4132bdd771d93dd44e68
出典データセット
uspto-grants-2008_07
特許番号
US07393873B2

関連ノート

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