pentanimidamide

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

Procedure: 1.41 kg of valeroamidine and 1.41 kg of diethyl acetylsuccinate were dissolved in 4.5 L of methanol and 1.16 kg of potassium hydroxide was added thereto. The mixture was stirred for 15 hours at room temperature, and then 14 L of water was added while stirring. The obtained solid was filtered, dried, and dissolved in 6 L of ethanol. Then, 840 g of thionyl chloride was added by drop for 2 hours and stirred for 12 hours at 60° C. To this mixture was added a solution of 1.22 kg of sodium bicarbonate in 15 L of water and the produced solid was filtered and dried to obtain 1.35 kg (47.8% yield) of the titled compound. while stirring The obtained solid was filtered dried dissolved in 6 L of ethanol Then, 840 g of thionyl chloride was added by drop for 2 hours stirred for 12 hours at 60° C To this mixture was added a solution of 1.22 kg of sodium bicarbonate in 15 L of water the produced solid was filtered dried

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

Procedure: To a solution of ethyl 2-acetyl-5,5-dimethyl-4-oxohexanoate (1.04 g) and pentanimidamide (0.89 g) in methanol (10 mL) was added 28% sodium methoxide-methanol solution (3.7 mL), and the mixture was stirred at room temperature for 24 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (0.34 g, 36%). the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated the residue was purified by silica gel column chromatography

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

Procedure: To a solution of ethyl 2-acetyl-5,5-dimethyl-4-oxohexanoate (1.04 g) and pentanimidamide (0.89 g) in methanol (10 mL) was added 28% sodium methoxide-methanol solution (3.7 mL), and the mixture was stirred at room temperature for 24 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (0.34 g, 36%). the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated the residue was purified by silica gel column chromatography

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

Procedure: 1.41 kg of valeroamidine and 1.41 kg of diethyl acetylsuccinate were dissolved in 4.5 L of methanol and 1.16 kg of potassium hydroxide was added thereto. The mixture was stirred for 15 hours at room temperature, and then 14 L of water was added while stirring. The obtained solid was filtered, dried, and dissolved in 6 L of ethanol. Then, 840 g of thionyl chloride was added by drop for 2 hours and stirred for 12 hours at 60° C. To this mixture was added a solution of 1.22 kg of sodium bicarbonate in 15 L of water and the produced solid was filtered and dried to obtain 1.35 kg (47.8% yield) of the titled compound. while stirring The obtained solid was filtered dried dissolved in 6 L of ethanol Then, 840 g of thionyl chloride was added by drop for 2 hours stirred for 12 hours at 60° C To this mixture was added a solution of 1.22 kg of sodium bicarbonate in 15 L of water the produced solid was filtered dried