Isoamyl Nitrite → 4-Cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

HRID 1990072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1990072
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:14]([F:17])([F:16])[F:15])=[C:9]([C:12]#[N:13])[C:10]=1N)=[O:5])[CH3:2].[I:18]C1CC(C(C)C)CCC1(I)C.N(OCCC(C)C)=O>CC#N>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:14]([F:17])([F:16])[F:15])=[C:9]([C:12]#[N:13])[C:10]=1[I:18])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 8053Isoamyl NitriteHCID 685236583-Amino-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl esterHCID 86612408Diiodomenthane

Produkt 1

HCID 685208084-Cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Combine 3-amino-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester, prepared in preparation 45, (1.12 mmol), diiodomenthane (3.92 mmol), and isoamyl nitrite (2.8 mmol) in CH3CN and heat to 80° C. After 45 minutes, cool to room temperature and concentrate in vacuo. Purify the dark residue by flash chromatography eluting with methylene chloride. Concentration of desired fractions and recrystallization from hexanes provides the title compound: 1H NMR (400 MHz, CDCl3) δ 4.45 (q, 2H, J=7.2 Hz) and 1.44 (t, 3H, J=7.3 Hz), 19F NMR (CDCl3) δ—57.6 ppm (s).

Aufarbeitung

  1. temperaturecool to room temperature
  2. concentrationconcentrate in vacuo
  3. customPurify the dark residue by flash chromatography
  4. washeluting with methylene chloride
  5. customConcentration of desired fractions and recrystallization from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4b3d1d8f2561494594ef4e0ec7eaab49
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642361B2

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