4-((4-Fluorophenyl)sulfonyl)aniline → HCID 12011164, Verbindung

HRID 1795785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795785
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:18]([O-])=O.[Na+]>Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 5728144-((4-Fluorophenyl)sulfonyl)anilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 12011164HCID 12011164, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-[(4-fluorophenyl)sulfonyl]phenylamine (IV, Step II, 3.10 g, 12.3 mmol) in concentrated hydrochloric acid (30 mL) at 0° is treated with sodium nitrite (934 mg, 13.5 mmol) in H2O (15 mL). After 30 min, the mixture is treated with stannous chloride (5.57 g, 24.7 mmol) in concentrated hydrochloric acid (15 mL). The mixture is stirred at 0° for 1 hr, and then at 20–25° for 1 hr. The precipitate is collected and slurried in H2O. The mixture is made basic (sodium hydroxide, 50%) and the solid isolated. The material is partitioned between methylene chloride and saline. The organic layer is dried, filtered, and concentrated under reduced pressure to give the title compound, NMR (300 MHz, CDCl3) 7.85–7.95, 7.74, 7.13, 6.85, 5.64 and 3.65 δ.

Aufarbeitung

  1. waitat 20–25° for 1 hr
  2. customThe precipitate is collected
  3. customthe solid isolated
  4. customThe material is partitioned between methylene chloride and saline
  5. customThe organic layer is dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ffe2327715c14ff6a16b7e5525651f52
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030109B2

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