Sodium Hydroxide → HCID 1471779, Verbindung

HRID 865731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 865731
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=2[C:17]#[N:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[C:17]#[N:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 706762HCID 706762, Verbindung

Produkt 1

HCID 1471779HCID 1471779, VerbindungAusbeute 904,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred slurry of 4-nitro-2-cyanophenyl phenyl sulfide (13.3 g, 5.19 mmol) and 100 mL of absolute ethanol was added stannous chloride dihydrate (58.6 g, 26 mmol) in one portion. The mixture was heated to 60° C. where an exothermic reaction caused the solution to strongly reflux. The mixture was allowed to stir at ambient temperature for 30 min., poured onto ice-water and made strongly basic by the addition of 350 mL of 15% NaOH. The mixture was extracted with methylene chloride (4×275 mL), the extracts dried (MgSO4), filtered, and the solvent removed in vacuo to yield an oil which was chromatographed on 300 g of silica gel using a methylene chloride (20%, 40%, 60% 80% and 100%) in hexane gradient. The proper fractions were combined and the solvent removed to yield the 4-amino-2-cyano-phenyl phenyl sulfide (10.62 g, 91%) as a pale yellow solid; mp 73°-75° C. 1H-NMR (300 MHz, CDCl3): 4.01 (s, 2H, NH2), 6.78 (dd 1H, J=8.5, 2.6, aromatic), 6.95 (d, 1H, J=2.6, aromatic), 7.18-7.29 (m, 5H, aromatic), 7.34 (d, 1H, J=8.5, aromatic). MS (CI, CH4): 227(M+1).

Aufarbeitung

  1. customan exothermic reaction
  2. temperatureto strongly reflux
  3. additionpoured onto ice-water
  4. extractionThe mixture was extracted with methylene chloride (4×275 mL)
  5. dry with materialthe extracts dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customto yield an oil which
  9. customwas chromatographed on 300 g of silica gel using a methylene chloride (20%, 40%, 60% 80% and 100%) in hexane gradient
  10. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-89a9d163c19942b580caf6a36405a152
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05567735

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