Calcium Carbonate → 6-Chloro-2-iodopyridin-3-amine

HRID 225751

Reaktionsgleichung

Reaktionsgleichung von HRID 225751
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Ca+2].[I:14](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>ClCCl.CO>[NH2:1][C:2]1[C:7]([I:14])=[N:6][C:5]([Cl:8])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 10112Calcium CarbonateHCID 793055-Amino-2-chloropyridineHCID 56924451Trimethylbenzylammonium Dichloroiodate

Produkt 1

HCID 184070436-Chloro-2-iodopyridin-3-amineAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

23.2 g (180.5 mM) of 5-amino-2-chloropyridine are mixed in 70 ml of dichloro-methane (DCM) and 180 ml of methanol, and 21.6 g (216 mM) of calcium carbonate and 75.3 g (226 mM) of benzyltrimethylammonium dichloroiodate are added. The reaction mixture is stirred at room temperature for 16 hours, and then filtered to remove the mineral salts. The filtrate is diluted with water and extracted with DCM. The organic phase obtained is washed with sodium chloride solution, and then with saturated sodium thiosulfate solution, dried over magnesium sulfate and concentrated under reduced pressure. An oil is obtained, which is purified by chromatography on silica gel, eluting with a cyclohexane/ethyl acetate mixture (80/20 and then 70/30; v/v). 13.9 g of the expected product are thus obtained in the form of an orange-colored solid (yield=30%).

Aufarbeitung

  1. filtrationfiltered
  2. customto remove the mineral salts
  3. additionThe filtrate is diluted with water
  4. extractionextracted with DCM
  5. customThe organic phase obtained
  6. washis washed with sodium chloride solution
  7. dry with materialwith saturated sodium thiosulfate solution, dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customAn oil is obtained
  10. customwhich is purified by chromatography on silica gel
  11. washeluting with a cyclohexane/ethyl acetate mixture (80/20

Quellen und Nachweise

ORD-Eintrag
ord-8f3a0f97afd14c4d9c61cd32c024c2b9
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557122B2

Verknüpfte Notizen

Wird geladen…