Ethyl Acetate → Methyl 6-chloro-5-isothiocyanatonicotinate

HRID 1426162

Reaktionsgleichung

Reaktionsgleichung von HRID 1426162
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[C:7]([Cl:16])=[N:8][CH:9]=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>ClCCl>[Cl:16][C:7]1[C:6]([N:5]=[C:1]=[S:2])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 18412438Methyl 5-amino-6-chloropyridine-3-carboxylate

Produkt 1

HCID 86639699Methyl 6-chloro-5-isothiocyanatonicotinateAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Thiophosgene (6.367 g, 55.37 mmol) in dichloromethane (10 mL) was added to a mixture of methyl 5-amino-6-chloronicotinate (8.61 g, 46.14 mmol) and sodium carbonate (9.781 g, 92.29 mmol) in dichloromethane (200 mL). The reaction mixture was stirred for four days at ambient temperature. The reaction mixture was washed with water and brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with 12:1 hexane:ethyl acetate to afford methyl 6-chloro-5-isothiocyanatonicotinate (8.03 g, 76.1% yield) as a white solid: 1H NMR (CDCl3) δ 3.97 (s, 3H), 8.09 (s, 1H), 8.84 (s, 1H).

Aufarbeitung

  1. washThe reaction mixture was washed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified via MPLC (Biotage)
  5. washeluting with 12:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-0a7ff6a18d04445fb83ada702e8df418
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933077B2

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