Methyl iodide → 4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(2-methoxy-5-methoxymethylphenyl)-N-propylamino]thiazole hydrochloride

HRID 1698871

Reaktionsgleichung

Reaktionsgleichung von HRID 1698871
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]([N:16]([C:20]2[CH:25]=[C:24]([CH2:26][OH:27])[CH:23]=[CH:22][C:21]=2[O:28][CH3:29])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15].[H-].[Na+].[CH3:32]I>CN(C)C=O.C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]([N:16]([C:20]2[CH:25]=[C:24]([CH2:26][O:27][CH3:32])[CH:23]=[CH:22][C:21]=2[O:28][CH3:29])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 183222484-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-hydroxymethyl-2-methoxyphenyl)-N-propylamino]thiazole

Produkt 1

HCID 183222644-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(2-methoxy-5-methoxymethylphenyl)-N-propylamino]thiazole hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

At 0° C., under an inert atmosphere, 320 mg of 4-(2-chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-hydroxymethyl-2-methoxyphenyl)-N-propylamino]thiazole are dissolved in 0.7 ml of dimethylformamide. 70 mg of sodium hydride (50% in oil) are added. After 5 minutes, 0.24 ml of methyl iodide is added. After 12 hours at room temperature, the reaction mixture is diluted with ethyl acetate and then hydrolyzed. The organic phase is washed several times with water before being dried over sodium sulphate. After purification on a silica gel; the expected product is dissolved in dichloromethane. A 0.1 N solution of hydrochloric acid in isopropanol is then added. After evaporation under vacuum, the expected product is obtained in hydrochloride form; m.p.=71° C.

Aufarbeitung

  1. waitAfter 12 hours at room temperature
  2. washThe organic phase is washed several times with water
  3. dry with materialbefore being dried over sodium sulphate
  4. customAfter purification on a silica gel
  5. dissolutionthe expected product is dissolved in dichloromethane
  6. additionA 0.1 N solution of hydrochloric acid in isopropanol is then added
  7. customAfter evaporation under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1079f1e2cc3b41d8889f99e8fffd3c48
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344470B1

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