1-bromo-2-ethylsulfanylethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-amino-3-nitrophenol (17.5 g.) in ethanol (300 ml.) was treated with solid potassium hydroxide (6.38 g.). The mixture was treated with a solution of 2 -bromoethyl ethyl thioether (21.2 g.) in ethanol (100 ml.), and stirred at room temperature for 4 hours. The reaction mixture was then concentrated in vacuo and the residue was dissolved in chloroform (200 ml.). The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.), dried over magnesium sulphate and evaporated to give 4-[2-(ethylthio)ethoxy]-2-nitroaniline (23.4 g.) in the form of a dark red oil, which was used in the next stage without further purification being necessary. The reaction mixture was then concentrated in vacuo the residue was dissolved in chloroform (200 ml.) The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.) dried over magnesium sulphate evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-amino-3-nitrophenol (17.5 g.) in ethanol (300 ml.) was treated with solid potassium hydroxide (6.38 g.). The mixture was treated with a solution of 2 -bromoethyl ethyl thioether (21.2 g.) in ethanol (100 ml.), and stirred at room temperature for 4 hours. The reaction mixture was then concentrated in vacuo and the residue was dissolved in chloroform (200 ml.). The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.), dried over magnesium sulphate and evaporated to give 4-[2-(ethylthio)ethoxy]-2-nitroaniline (23.4 g.) in the form of a dark red oil, which was used in the next stage without further purification being necessary. The reaction mixture was then concentrated in vacuo the residue was dissolved in chloroform (200 ml.) The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.) dried over magnesium sulphate evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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%). cooling washed with water dried over anhydrous magnesium sulfate distilled under reduced pressure to remove the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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%). cooling washed with water dried over anhydrous magnesium sulfate distilled under reduced pressure to remove the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-amino-3-nitrophenol (17.5 g.) in ethanol (300 ml.) was treated with solid potassium hydroxide (6.38 g.). The mixture was treated with a solution of 2 -bromoethyl ethyl thioether (21.2 g.) in ethanol (100 ml.), and stirred at room temperature for 4 hours. The reaction mixture was then concentrated in vacuo and the residue was dissolved in chloroform (200 ml.). The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.), dried over magnesium sulphate and evaporated to give 4-[2-(ethylthio)ethoxy]-2-nitroaniline (23.4 g.) in the form of a dark red oil, which was used in the next stage without further purification being necessary. The reaction mixture was then concentrated in vacuo the residue was dissolved in chloroform (200 ml.) The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.) dried over magnesium sulphate evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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%). cooling washed with water dried over anhydrous magnesium sulfate distilled under reduced pressure to remove the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-amino-3-nitrophenol (17.5 g.) in ethanol (300 ml.) was treated with solid potassium hydroxide (6.38 g.). The mixture was treated with a solution of 2 -bromoethyl ethyl thioether (21.2 g.) in ethanol (100 ml.), and stirred at room temperature for 4 hours. The reaction mixture was then concentrated in vacuo and the residue was dissolved in chloroform (200 ml.). The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.), dried over magnesium sulphate and evaporated to give 4-[2-(ethylthio)ethoxy]-2-nitroaniline (23.4 g.) in the form of a dark red oil, which was used in the next stage without further purification being necessary. The reaction mixture was then concentrated in vacuo the residue was dissolved in chloroform (200 ml.) The chloroform solution was washed with aqueous sodium bicarbonate solution (10% w/v; 200 ml.) dried over magnesium sulphate evaporated