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

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Reaction Steps

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), 2-bromoethyl ethyl sulfide (1.01 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 4 hours. 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-(2-ethylthioethyl)pyrrol-2-yl]thiazole (2.01 g, yield: 89%).

Provenance & Evidence