Thiophenol → 4-Aminomethyl-2-fluoro-benzonitrile

HRID 1717493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717493
C1(S)C=CC=CC=1.C(N(CC)CC)C.[N:15]([CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([F:27])[CH:20]=1)=[N+]=[N-]>C(#N)C>[NH2:15][CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([F:27])[CH:20]=1

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 219046434-Azidomethyl-2-fluorobenzonitrile

Produkt 1

HCID 219046524-Aminomethyl-2-fluoro-benzonitrileAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a suspension of stannous chloride dihydrate (0.45 g, 2.4 mmol) in 20 mL of acetonitrile under stirring was added thiophenol (1.07 g, 9.7 mmol) and triethylamine (0.726 g, 7.17 mmol). Thereafter was added a solution of 4-azidomethyl-2-fluorobenzonitrile (0.279 g, 1.58 mmol; see step (iv) above) in a few mLs of acetonitrile. After 1.5 h, the azide was consumed and the solvent was evaporated. The residue was dissolved in methylene chloride and washed three times with 2M NaOH. The organic phase was extracted twice with 1M HCl. The combined acidic aqueous phase washed with methylene chloride and then made alkaline with 2M NaOH and extracted three times with methylene chloride. The organic phase was dried (Na2SO4) and evaporated to give 0.172 g (72%) of the desired sub-title compound which could be used without purification.

Aufarbeitung

  1. customthe azide was consumed
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed three times with 2M NaOH
  5. extractionThe organic phase was extracted twice with 1M HCl
  6. washThe combined acidic aqueous phase washed with methylene chloride
  7. extractionextracted three times with methylene chloride
  8. dry with materialThe organic phase was dried (Na2SO4)
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8b9181ce928448f8b277f1b459c8b066
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803954B2

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