Iodoethane → 4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-ethoxycarbonyl-2-methoxyphenyl)-N-propylamino]thiazole hydrochloride

HRID 1698868

Reaktionsgleichung

Reaktionsgleichung von HRID 1698868
[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]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][C:21]=2[O:29][CH3:30])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:37](I)[CH3:38]>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]([C:26]([O:28][CH2:37][CH3:38])=[O:27])[CH:23]=[CH:22][C:21]=2[O:29][CH3:30])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15]

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 183222624-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-carboxy-2-methoxyphenyl)-N-propylamino]thiazole

Produkt 1

HCID 183222474-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-ethoxycarbonyl-2-methoxyphenyl)-N-propylamino]thiazole hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1 g of 4-(2-chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-carboxy-2methoxyphenyl)-N-propylamino]thiazole (EXAMPLE 3) is dissolved at room temperature and under argon in 3 ml of dimethylformamide and then 0.66 g of Cs2CO3 and 0.5 ml of ethyl iodide are added. The reaction mixture is stirred for one hour and then diluted with ethyl acetate. It is washed with water, dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on a silica gel column eluted with a cyclohexane/ethyl acetate 5/1 (v/v) mixture. The expected product is obtained in the form of a colourless oil.

Aufarbeitung

  1. washIt is washed with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated to dryness
  4. customThe residue is purified by chromatography on a silica gel column
  5. washeluted with a cyclohexane/ethyl acetate 5/1 (v/v) mixture

Quellen und Nachweise

ORD-Eintrag
ord-37ee00064d1e4c8ab4b2bc1d16616d30
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344470B1

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