Water → 3-Chloro-4-(methylamino)benzonitrile

HRID 1348907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1348907
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[CH3:11][NH2:12].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:12][CH3:11])[C:5]#[N:6]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6329MethylamineHCID 1455253-Chloro-4-fluorobenzonitrile

Produkt 1

HCID 159077543-Chloro-4-(methylamino)benzonitrileAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 3-chloro-4-fluorobenzonitrile (5.2 g, 33 mmol), THF (55 mL), and 40% methylamine in water (25 mL, 290 mmol) in a sealed tube was heated to 65° C. for 1.5 hours, cooled to room temperature. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5 to provide 6.3 g (95%) of the desired product. MS (DCI/NH3) m/z 184, 186 (M+H+NH3)+; 1H NMR (DMSO-d6) δ 7.72 (d, 1H), 7.55 (dd, 1H), 6.70 (d, 1H), 6.52 (br q, 1H), 2.80 (d, 3H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dry with materialThe resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5

Quellen und Nachweise

ORD-Eintrag
ord-45fc71d0235945cebc01eed26239e3a8
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211595B2

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