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

HRID 746741

Reaktionsgleichung

Reaktionsgleichung von HRID 746741
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-02c64c4ec5bc4132bdd771d93dd44e68
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393873B2

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