Methyl nitrite → Alpha-Oximino-2-Thienylacetonitrile

HRID 1835025

Reaktionsgleichung

Reaktionsgleichung von HRID 1835025
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].[OH-].[Na+].[N:11](OC)=[O:12]>CO>[OH:12][N:11]=[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]#[N:8]

Komponenten

5

Edukt 3

HCID 12231Methyl nitriteHCID 14798Sodium HydroxideHCID 728802-Thienylacetonitrile

Produkt 1

HCID 73667355Alpha-Oximino-2-ThienylacetonitrileAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

As described under 3.1, 86 g (0.7 mol) of thiophene-2-acetonitrile are charged, with stirring and in the presence of 28 g (0.7 mol) of sodium hydroxide in 210 ml of methanol, with 0.7 mol of gaseous methyl nitrite at 0-5° C. over 4.5 hours. The ice bath is then removed and the brown solution is stirred overnight at room temperature. The solvent is distilled off and the residue is charged with water and toluene. The aqueous phase is separated, washed twice with ethyl acetate and acidified with conc. HCl. The aqueous phase is extracted twice with toluene, the extracts are washed with water and dried over magnesium sulfate. After filtration, the solvent is distilled off and the remaining brown solid is recrystallised from toluene, giving 28.6 g (39% of theory) of α-hydroxyiminothiophene-2-acetonitrile in the form of a beige solid having a melting point of 105-109° C. The 1H-NMR spectrum is consistent with the proposed structure.

Aufarbeitung

  1. additionare charged
  2. customThe ice bath is then removed
  3. distillationThe solvent is distilled off
  4. additionthe residue is charged with water and toluene
  5. customThe aqueous phase is separated
  6. washwashed twice with ethyl acetate
  7. extractionThe aqueous phase is extracted twice with toluene
  8. washthe extracts are washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationAfter filtration
  11. distillationthe solvent is distilled off
  12. customthe remaining brown solid is recrystallised from toluene

Quellen und Nachweise

ORD-Eintrag
ord-59c30691e51d41b2a39b294baa8eb9ac
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770420B2

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