Ether, bis(1-chloroethyl) → 6-Chloro-5-methoxymethoxy-nicotinonitrile

HRID 1471581

Reaktionsgleichung

Reaktionsgleichung von HRID 1471581
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.Cl[CH:21]([O:23][CH:24](C)Cl)C>C(Cl)Cl>[Cl:1][C:2]1[C:9]([O:10][CH2:21][O:23][CH3:24])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 23419Ether, bis(1-chloroethyl)HCID 81531DiisopropylethylamineHCID 866364556-Chloro-5-hydroxynicotinonitrile

Produkt 1

HCID 866364566-Chloro-5-methoxymethoxy-nicotinonitrileAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-5-hydroxy-nicotinonitrile (1.12 g, 7.24 mmol) in DCM (15 mL) was added N,N-diisopropyl ethylamine (1.57 mL, 9.05 mmol) followed by the addition of chloro-methyl methylether (0.66 mL, 8.69 mmol) slowly at 0° C. After overnight at room temperature, the reaction mixture was washed with saturated NaHCO3 (10 mL) and brine (10 mL), dried over Na2SO4, filtered, and concentrated to give yellow oil. Purification was accomplished by flash chromatography on silica gel using 5-25% EtOAc/hexanes gradient elution to yield the title compound (0.68 g, 50%) as a transparent oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.53 (d, J=2.0 Hz, 1 H), 8.14 (d, J=2.0 Hz, 1 H), 5.42 (s, 2 H), 3.40 (s, 3H); MS (ES) m/z: 199 (M+1)+.

Aufarbeitung

  1. washthe reaction mixture was washed with saturated NaHCO3 (10 mL) and brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give yellow oil
  6. customPurification
  7. washwas accomplished by flash chromatography on silica gel using 5-25% EtOAc/hexanes gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-da2f4ab1ca4f483a8a11a2fa93d448bd
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012431B2

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