(4-tert-butylphenyl)methanethiol

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

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

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: Into a 25 mL round bottom flask is introduced 2-ethylsulfinyl-3-((2-tetrahydropyranyloxy)methyl) chromen-4-one (5 g, 14.87 mmol). Acetonitrile is then added to it followed by 4-tertbutylbenzyl mercaptan (74.3 mmol). The reaction mixture is stirred for 10 hours at room temperature after which the solvent is removed in vacuo. The crude residue obtained is purified by silica gel chromatography (ethyl acetate:hexanes) to obtain the product. is removed in vacuo

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

Procedure: Sodium hydroxide 0.22 g was dissolved in 5 ml of water, and thereto were added 10 ml of dichloromethane, 1.55 g of 2-tert.-butyl-4,5-dibromo-3(2H)-pyridazinone and 0.05 g of triethylbenzylammonium chloride. The resulting solution was incorporated with 0.83 g of 4-tert.-butyl-benzyl mercaptan at room temperature and then stirred for 10 hours. After completion of the reaction, about 50 ml of CH2Cl2 was added to the solution and the organic layer was separated therefrom, washed with 5% aqueous solution of sodium hydroxide and then with water, and dried over anhydrous sodium sulfate. Solvent was distilled away therefrom under reduced pressure and the resulting solid residue was recrystallized from a benzene/n-hexane mixed solvent to obtain 1.32 g of the intended compound (yield: 65%). was added to the solution the organic layer was separated washed with 5% aqueous solution of sodium hydroxide with water, and dried over anhydrous sodium sulfate Solvent was distilled away under reduced pressure and the resulting solid residue was recrystallized from a benzene/n-hexane mixed solvent

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

Procedure: To 3 ml of dry N,N-dimethylformamide was added 0.024 g of 55% sodium hydride. The resulting mixture was kept at 0° C. and was added dropwise with a solution of 1 g of p-t-butylbenzyl mercaptan dissolved in 5 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution of 0.67 g of 5-chloro-2-ethyl-4-methyl-3(2H)-pyridazinone dissolved in 5 ml of N,N-dimethylformamide. After completion of dropwise addition, the resulting mixture was allowed to stand over night. The resulting solution was poured into 30 ml of water and extracted twice with 30 ml of diethyl ether. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and freed of solvent by distillation under reduced pressure to give 1.42 g of a crude product. The crude product was separated and purified by thin layer chromatography (silica gel, benzene) to obtain 0.69 g of 5-(p-t-butylbenzylthio)-2-ethyl-4-methyl-3(2H)-pyridazinone. was kept at 0° C. After ten minutes passed After completion of dropwise addition to stand over night extracted twice with 30 ml of diethyl ether The resulting organic layer was washed with water dried over anhydrous sodium sulfate freed of solvent by distillation under reduced pressure to give 1.42 g of a crude product The crude product was separated purified by thin layer chromatography (silica gel, benzene)

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

Procedure: To 3 ml of dry N,N-dimethylformamide was added 0.024 g of 55% sodium hydride. The resulting mixture was kept at 0° C. and was added dropwise with a solution of 1 g of p-t-butylbenzyl mercaptan dissolved in 5 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution of 0.67 g of 5-chloro-2-ethyl-4-methyl-3(2H)-pyridazinone dissolved in 5 ml of N,N-dimethylformamide. After completion of dropwise addition, the resulting mixture was allowed to stand over night. The resulting solution was poured into 30 ml of water and extracted twice with 30 ml of diethyl ether. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and freed of solvent by distillation under reduced pressure to give 1.42 g of a crude product. The crude product was separated and purified by thin layer chromatography (silica gel, benzene) to obtain 0.69 g of 5-(p-t-butylbenzylthio)-2-ethyl-4-methyl-3(2H)-pyridazinone. was kept at 0° C. After ten minutes passed After completion of dropwise addition to stand over night extracted twice with 30 ml of diethyl ether The resulting organic layer was washed with water dried over anhydrous sodium sulfate freed of solvent by distillation under reduced pressure to give 1.42 g of a crude product The crude product was separated purified by thin layer chromatography (silica gel, benzene)

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

Procedure: To 3 ml of dry N,N-dimethylformamide was added 0.024 g of 55% sodium hydride. The resulting mixture was kept at 0° C. and was added dropwise with a solution of 1 g of p-t-butylbenzyl mercaptan dissolved in 5 ml of N,N-dimethylformamide. After ten minutes passed, the resulting mixture was added dropwise with a solution of 0.67 g of 5-chloro-2-ethyl-4-methyl-3(2H)-pyridazinone dissolved in 5 ml of N,N-dimethylformamide. After completion of dropwise addition, the resulting mixture was allowed to stand over night. The resulting solution was poured into 30 ml of water and extracted twice with 30 ml of diethyl ether. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and freed of solvent by distillation under reduced pressure to give 1.42 g of a crude product. The crude product was separated and purified by thin layer chromatography (silica gel, benzene) to obtain 0.69 g of 5-(p-t-butylbenzylthio)-2-ethyl-4-methyl-3(2H)-pyridazinone. was kept at 0° C. After ten minutes passed After completion of dropwise addition to stand over night extracted twice with 30 ml of diethyl ether The resulting organic layer was washed with water dried over anhydrous sodium sulfate freed of solvent by distillation under reduced pressure to give 1.42 g of a crude product The crude product was separated purified by thin layer chromatography (silica gel, benzene)

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

Procedure: To 30 ml of dry tetrahydrofuran was added 0.5 g of 55% sodium hydride. The resulting mixture was kept at room temperature and added dropwise with a solution of 1.8 g of p-t-butylbenzyl mercaptan dissolved in 10 ml of tetrahydrofuran. After ten minutes passed, the resulting mixture was added dropwise with a solution of 2.0 g of 2-t-butyl-5-chloro-4-methyl-3(2H)-pyridazinone dissolved in 10 ml of tetrahydrofuran. After completion of dropwise addition, the resulting mixture was reacted for 2 hours under heat-reflux. After the reaction mixture was concentrated under reduced pressure, it was poured into 50 ml of water and extracted twice with 50 ml of diethyl ether. The resulting organic layer was dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give 3.5 g of crude product. The crude product was recrystallized from 5 ml of hexane to obtain 1.6 g of 2-t-butyl-5-(p-t-butylbenzylthio)-4-methyl-3(2H)-pyridazinone. was kept at room temperature After ten minutes passed After completion of dropwise addition the resulting mixture was reacted for 2 hours under heat-reflux After the reaction mixture was concentrated under reduced pressure, it was poured into 50 ml of water extracted twice with 50 ml of diethyl ether The resulting organic layer was dried over anhydrous sodium sulfate freed of solvent by distillation under reduced pressure to give 3.5 g of crude product The crude product was recrystallized from 5 ml of hexane

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-tert-butyl-4-tert-butyldimethylsilyloxymethyl-5-chloro 3(2H)-pyridazinone (1.5 g, 4.54 mmol) in DMF (10 ml) is added anhydrous cesium carbonate (2.9 g, 9.09 mmol) and 4-tert-butybenzyl mercaptan (1.02 g, 4.54 mmol). The mixture is stirred for 2 hours at 70° C. and then cooled to room temperature and ethyl acetate is added to it. The solution is then washed with water, dried and concentrated and the residue subjected to purification by flash chromatography (silica gel; ethyl acetate/hexanes) to give the above compound. cooled to room temperature The solution is then washed with water dried concentrated the residue subjected to purification by flash chromatography (silica gel; ethyl acetate/hexanes) to give the above compound

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

Procedure: Into a 25 mL round bottom flask is introduced 2-ethylsulfinyl-3-((2-tetrahydropyranyloxy)methyl) chromen-4-one (5 g, 14.87 mmol). Acetonitrile is then added to it followed by 4-tertbutylbenzyl mercaptan (74.3 mmol). The reaction mixture is stirred for 10 hours at room temperature after which the solvent is removed in vacuo. The crude residue obtained is purified by silica gel chromatography (ethyl acetate:hexanes) to obtain the product. is removed in vacuo