4-fluorobenzenecarbothioamide

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: The title compound was prepared according to the method of Scheme II in a manner analogous to Example 31 except 4-fluorothiobenzamide was used instead of thiobenzamide and 2-chloro-2-phenylacetyl chloride was used instead of 2-bromopropionate.

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

Procedure: The title compound was prepared according to the method of Scheme II in a manner analogous to Example 31 except 4-fluorothiobenzamide was used instead of thiobenzamide and 2-chloro-2-phenylacetyl chloride was used instead of 2-bromopropionate.

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

Procedure: To a solution of p-fluorothiobenzamide (0.39 g, 2.5 mmol) in 20 mL of abs. EtOH is added 2,4′-dibromoacetophenone (0.7 g, 2.5 mmol) all at once. The reaction mixture is stirred at room temperature for 3 hours and then chilled in ice bath. The precipitate is collected by filtration, washed with cold EtOH (5 ml×2) and dried in vacuum to give 2-(4′-fluorophenyl)-4-(4′-bromophenyl)thiazole as a white fluffy crystaline solid (1.55 g, 93%). mp.158-9° C. chilled in ice bath The precipitate is collected by filtration washed with cold EtOH (5 ml×2) dried in vacuum

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

Procedure: To a solution of the crude product of 4-fluorothiobenzamide (2.0 g, 12.9 mmol) in EtOH (30 ml) is added 2-bromo-4′ methylacetophenone (2.75 g, 12.9 mmol). The mixture is heated to reflux for 24 hours. The course of the reaction is followed by thin layer chromatography. Upon completion of the reaction the solution is cooled to room temperature and the white precipitate filtered and dried under vacuum to yield 2-(4′-fluorophenyl)-4-(p-tolyl) thiazole (1.54 g, 54%). The mixture is heated to reflux for 24 hours Upon completion of the reaction the solution the white precipitate filtered dried under vacuum

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

Procedure: To a solution of the crude product of 4-fluorothiobenzamide (2.0 g, 12.9 mmol) in EtOH (30 ml) is added 2-bromo-4′ methylacetophenone (2.75 g, 12.9 mmol). The mixture is heated to reflux for 24 hours. The course of the reaction is followed by thin layer chromatography. Upon completion of the reaction the solution is cooled to room temperature and the white precipitate filtered and dried under vacuum to yield 2-(4′-fluorophenyl)-4-(p-tolyl) thiazole (1.54 g, 54%). The mixture is heated to reflux for 24 hours Upon completion of the reaction the solution the white precipitate filtered dried under vacuum

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

Procedure: 4-Fluorobenzamide (5.0 g, 35.9 mmol) in benzene (100 ml) is added Lawesson's reagent (7.27 g, 18.0 mmol) and the resulting solution is heated to reflux for 1 hour. The solution is cooled to room temperature, concentrated and water (150 ml) added. The mixture is heated to reflux for 3 hours, and cooled to room temperature. The precipitate is filtered and dried under vacuum to yield 4-fluorothiobenzamide as a yellow solid (4.1 g, 71%). the resulting solution is heated to reflux for 1 hour concentrated water (150 ml) added The mixture is heated to reflux for 3 hours cooled to room temperature The precipitate is filtered dried under vacuum

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

Procedure: To a solution of p-fluorothiobenzamide (0.39 g, 2.5 mmol) in 20 mL of abs. EtOH is added 2,4′-dibromoacetophenone (0.7 g, 2.5 mmol) all at once. The reaction mixture is stirred at room temperature for 3 hours and then chilled in ice bath. The precipitate is collected by filtration, washed with cold EtOH (5 ml×2) and dried in vacuum to give 2-(4′-fluorophenyl)-4-(4′-bromophenyl)thiazole as a white fluffy crystaline solid (1.55 g, 93%). mp.158-9° C. 1H NMR (CDCl3): δ 7.16 (t, 2H), 7.47 (s, 1H), 7.58 (d, 2H), 7.87 ()d, 2H), 8.02 (m, 2H). chilled in ice bath The precipitate is collected by filtration washed with cold EtOH (5 ml×2) dried in vacuum

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

Procedure: To a solution of the crude product of 4-fluorothiobenzamide (2.0 g, 12.9 mmol) in EtOH (30 ml) is added 2-bromo-4′methylacetophenone (2.75 g, 12.9 mmol). The mixture is heated to reflux for 24 hours. The course of the reaction is followed by thin layer chromatography. Upon completion of the reaction the solution is cooled to room temperature and the white precipitate filtered and dried under vacuum to yield 2- (4′-fluorophenyl)-4- (p-tolyl) thiazole (1.54 g, 54%). 1H NMR (DMSOd6): δ 2.35 (s, 1H), 7.28 (d, 2H), 7.38 (t, 2H), 7.94 (d, 2H), 8.08 (dd, 2H), 8.11 (s, 1H). The mixture is heated to reflux for 24 hours Upon completion of the reaction the solution the white precipitate filtered dried under vacuum

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

Procedure: 4-Fluorobenzamide (5.0 g, 35.9 mmol) in benzene (100 ml) is added Lawesson's reagent (7,27 g, 18.0 mmol) and the resulting solution is heated to reflux for 1 hour. The solution is cooled to room temperature, concentrated and water (150 ml) added. The mixture is heated to reflux for 3 hours, and cooled to room temperature. The precipitate is filtered and dried under vacuum to yield 4-fluorothiobenzamide as a yellow solid (4.1 g, 71%). 1H NMR (CDCl3): δ 7.09 (t, 2H), 7.90(dd, 2H). the resulting solution is heated to reflux for 1 hour concentrated water (150 ml) added The mixture is heated to reflux for 3 hours cooled to room temperature The precipitate is filtered dried under vacuum

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

Procedure: 4-Fluorobenzamide (5.0 g, 35.9 mmol) in benzene (100 ml) is added Lawesson's reagent (7,27 g, 18.0 mmol) and the resulting solution is heated to reflux for 1 hour. The solution is cooled to room temperature, concentrated and water (150 ml) added. The mixture is heated to reflux for 3 hours, and cooled to room temperature. The precipitate is filtered and dried under vacuum to yield 4-fluorothiobenzamide as a yellow solid (4.1 g, 71%). 1H NMR (CDCl3): δ 7.09 (t, 2H), 7.90(dd, 2H). the resulting solution is heated to reflux for 1 hour concentrated water (150 ml) added The mixture is heated to reflux for 3 hours cooled to room temperature The precipitate is filtered dried under vacuum