1-(4-sulfanylphenyl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 4'-Mercaptoacetophenone ethylene acetal (0.656 g; obtained by the reaction of 4'-mercaptoacetophenone and ethylene glycol using an analogous procedure to that described in the third paragraph of the portion of Example 7 which is concerned with the preparation of starting materials) was added to a mixture of 2,4-dibromothiazole (0.82 g), potassium carbonate (0.468 g) and NMP (4 ml). The mixture was stirred and heated to 90° C. for 2.5 hours. The mixture was cooled to ambient temperature and partitioned between diethyl ether and brine. The organic phase was dried (MgSO4) and evaporated. The mixture was purified by column chromatography using a 3:1 mixture of ethyl acetate and petroleum ether as eluent. There was thus obtained 4'-[4-bromothiazole-2-ylthio]acetophenone ethylene acetal (1.1 g, 90%), m.p. 71° C.

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

Procedure: 4'-Mercaptoacetophenone ethylene acetal (0.656 g; obtained by the reaction of 4'-mercaptoacetophenone and ethylene glycol using an analogous procedure to that described in the third paragraph of the portion of Example 7 which is concerned with the preparation of starting materials) was added to a mixture of 2,4-dibromothiazole (0.82 g), potassium carbonate (0.468 g) and NMP (4 ml). The mixture was stirred and heated to 90° C. for 2.5 hours. The mixture was cooled to ambient temperature and partitioned between diethyl ether and brine. The organic phase was dried (MgSO4) and evaporated. The mixture was purified by column chromatography using a 3:1 mixture of ethyl acetate and petroleum ether as eluent. There was thus obtained 4'-[4-bromothiazole-2-ylthio]acetophenone ethylene acetal (1.1 g, 90%), m.p. 71° C.

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

Procedure: Using an analogous procedure to that described in Example 10, 4'-mercaptoacetophenone was reacted with 1-ethoxycarbonyl-3-(3-iodophenyl)-3-methoxypyrrolidine to give 3-[3-(4-acetylphenylthio)phenyl]-1-ethoxycarbonyl-3-methoxypyrrolidine as a gum in 24% yield.

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

Procedure: Using an analogous procedure to that described in Example 10, 4'-mercaptoacetophenone was reacted with 3-(3-iodophenyl)-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine hydrochloride to give 3-[3-(4-acetylphenylthio)phenyl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine as a gum in 75% yield.

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Using an analogous procedure to that described in Example 10, 4'-mercaptoacetophenone was reacted with 1-ethoxycarbonyl-3-(3-iodophenyl)-3-methoxypyrrolidine to give 3-[3-(4-acetylphenylthio)phenyl]-1-ethoxycarbonyl-3-methoxypyrrolidine as a gum in 24% yield.

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

Procedure: Using an analogous procedure to that described in Example 10, 4'-mercaptoacetophenone was reacted with 3-(3-iodophenyl)-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine hydrochloride to give 3-[3-(4-acetylphenylthio)phenyl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine as a gum in 75% yield.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 1-(4-mercaptophenyl)ethanone (0.76 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.218 g), stirred for 20 minutes and treated with 2-(cyclooctyloxy)ethyl methanesulfonate (1.25 g). The mixture was heated at 60° C. overnight, cooled, diluted with water, extracted twice with dichloromethane, and the organic layers were washed with water. The combined organic layers were dried (Na2SO4), filtered, and evaporated to give crude material which was purified by HPLC (dichloromethane-hexane-ethyl acetate; 48:48:4) to provide 1.08 g of 1-[4-[[2-(cyclooctyloxy)ethyl]thio]phenyl]ethanone as a colorless oil. cooled extracted twice with dichloromethane the organic layers were washed with water The combined organic layers were dried (Na2SO4) filtered evaporated to give crude material which was purified by HPLC (dichloromethane-hexane-ethyl acetate; 48:48:4)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 1-(4-mercaptophenyl)ethanone (1.2 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.350 g), stirred for 15 minutes and treated with the mesylate of 2-(2-naphthyloxy)ethanol (2.2 g). The mixture was heated at 60° C. for 2 hours and diluted with water and filtered. The solids were dissolve in dichloromethane, washed once with water, dried (Na2SO4), filtered and evaporated. Crystallization from dichloromethane-hexane provided 2.0 g of 1-[4-[[2-(2naphthalenyloxy)ethyl]thio]phenyl]ethanone, mp 151°-152° C. filtered The solids were dissolve in dichloromethane washed once with water dried (Na2SO4) filtered evaporated Crystallization from dichloromethane-hexane