Sodium Sulfate → 2-Phenoxy-6-(phenylamino)benzylamine

HRID 1826834

Reaktionsgleichung

Reaktionsgleichung von HRID 1826834
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]=1[C:10]#[N:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]=1[CH2:10][NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 221362262-Phenoxy-6-(phenylamino)benzonitrile

Produkt 1

HCID 221362242-Phenoxy-6-(phenylamino)benzylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product of example 1b above, 2-phenoxy-6-(phenylamino)benzonitrile, (0.4 g, 1.4 mmol) was dissolved in dry tetrahydrofuran (20 mL) and stirred under argon in a room temperature water bath. Lithium aluminum hydride (0.28 g, 7.0 mmol) was added in portions over 10 minutes. The reaction mixture was heated to 60° C. for 1 hour. The reaction mixture was cooled to room temperature and anhydrous sodium sulfate was added followed by quenching by the addition of a freshly prepared saturated solution of anhydrous sodium sulfate. The solvent was evaporated and the residue triturated with ethyl acetate, filtered and evaporated. Flash chromatography on silica gel eluted with 0–3% methanol in methylene chloride gave the title compound as a white amorphous solid. ES (+) MS m/e=274 (M−NH3)+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated to 60° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customby quenching by the addition of a freshly prepared saturated solution of anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue triturated with ethyl acetate
  6. filtrationfiltered
  7. customevaporated
  8. washFlash chromatography on silica gel eluted with 0–3% methanol in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-7beeab57cbbd4e90af9015636bac7921
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053099B1

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