Iodine → N-[2-(3-Iodo-7-methoxy-1-naphthyl)ethyl]acetamide

HRID 1856905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1856905
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[C:15]2[CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])=[CH:10][CH:9]=1.[I:24]I.I>O.C(O)(=O)C>[I:24][C:13]1[CH:14]=[C:15]([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[C:16]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([O:7][CH3:6])[CH:17]=2

Komponenten

7

Edukt 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 24841Hydrogen iodideHCID 82148Agomelatine

Produkt 1

HCID 22133330N-[2-(3-Iodo-7-methoxy-1-naphthyl)ethyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution is formed by adding 46.25 ml of glacial acetic acid and 1.25 ml of concentrated sulphuric acid to 2.5 ml of water. 2.5 g of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide (10.31 mmol) are dissolved in 30 ml of that solution. 2.09 g of iodine (8.25 mmol) and 0.91 g of HIO3 (5.16 mmol) are then added to the reaction mixture, causing a grey precipitate to appear in a solution that has turned red. The reaction mixture is heated for 15 hours at 65° C., 5.14 ml of concentrated hydriodic acid (13.41 mmol) are added and heating is continued for 2 hours. The suspension is then poured into 200 ml of water and the precipitate that forms is filtered off. The precipitate is dissolved in ethyl acetate and washed with 1M NaHCO3, the organic phase is then concentrated, and purified by chromatography on silica gel, using a dichloromethane/methanol mixture, 99.5/0.5, as eluant, to yield the title product.

Aufarbeitung

  1. customA solution is formed
  2. temperatureheating
  3. filtrationthe precipitate that forms is filtered off
  4. dissolutionThe precipitate is dissolved in ethyl acetate
  5. washwashed with 1M NaHCO3
  6. concentrationthe organic phase is then concentrated
  7. custompurified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1a4be8483b224d8fbe142c3b128bf815
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06143789

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