Sodium Hydroxide → Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(propoxymethyl)-1H-pyrrol-2-yl)-

HRID 542866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542866
[CH2:1]([O:4][CH2:5]Cl)[CH2:2][CH3:3].[OH-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]([C:30]3[NH:31][CH:32]=[CH:33][CH:34]=3)[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:13][CH:12]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:18]=[C:19]([C:30]3[N:31]([CH2:5][O:4][CH2:1][CH2:2][CH3:3])[CH:32]=[CH:33][CH:34]=3)[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:15][CH:16]=1

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 3063502Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)-HCID 109644311-(Chloromethoxy)propane

Produkt 1

HCID 3063492Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1-(propoxymethyl)-1H-pyrrol-2-yl)-Ausbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

4,5-Bis(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazole obtained in the same manner as described in Reference Example 6 (1.81 g, 5 mmole), chloromethyl n-propyl ether (0.65 g, 6 mmole), and tetra-n-butylammonium bromide (0.16 g, 0.5 mmole) are refluxed in two phases of benzene (20 ml) and 50% aqueous sodium hydroxide (20 ml) for 20 minutes. To the mixture are added water and benzene under ice-cooling, and the mixture is shaken. The benzene layer is taken, washed with water, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue is subjected to silica gel column chromatography (solvent, ethyl acetate:cyclohexane=1:20) to give oily 4,5-bis(4-methoxyphenyl)-2-(1-n-propoxymethylpyrrol-2-yl)thiazole (1.80 g, yield: 83%).

Aufarbeitung

  1. temperaturecooling
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-1a397368c6da4a98b7338c88d89d3cbb
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659726

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