1-amino-3-[3-(dimethylamino)propyl]thiourea

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

Procedure: A stirred solution of 7.05 g (0.04 mole) of 4-(3-dimethylaminopropyl)-3-thiosemicarbazide in 50 mL of absolute ethanol under nitrogen atmosphere was treated with 40 mL of 2N ethanolic hydrogen chloride and then with 6.6 g (0.04 mole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for 2 hr and heated at reflux for 5 hr. The reaction mixture was filtered hot to remove some crystalline sulfur and the filtrate solidified on cooling to give 8.3 g of crude product. After 5 recrystallizations from methyl ethyl ketone/methanol with charcoal treatment of the final recrystallization, a crystalline product was obtained, 3,4 g, mp 195°-196° C. After drying at 82° C. under reduced pressure, it was submitted for elemental analysis. heated at reflux for 5 hr The reaction mixture was filtered hot to remove some crystalline sulfur on cooling

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

Procedure: N-(3-dimethylaminopropyl)hydrazinecarbothioamide (0.12 g) was reacted with 5-nitro-2-furaldehyde (0.15 g) in 5 ml ethanol at reflux for 15 minutes. The mixture was cooled and treated with methanesulfonic acid (0.055 ml) and isopropanol and stored at 4° C. to give 0.15 g of the title compound as orange needles, mp 184°-187° C. at reflux for 15 minutes The mixture was cooled stored at 4° C.

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

Procedure: N-(3-dimethylaminopropyl)hydrazinecarbothioamide (0.12 g) was reacted with 5-nitro-2-furaldehyde (0.15 g) in 5 ml ethanol at reflux for 15 minutes. The mixture was cooled and treated with methanesulfonic acid (0.055 ml) and isopropanol and stored at 4° C. to give 0.15 g of the title compound as orange needles, mp 184°-187° C. at reflux for 15 minutes The mixture was cooled stored at 4° C.

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

Procedure: A stirred solution of 7.05 g (0.04 mole) of 4-(3-dimethylaminopropyl)-3-thiosemicarbazide in 50 mL of absolute ethanol under nitrogen atmosphere was treated with 40 mL of 2N ethanolic hydrogen chloride and then with 6.6 g (0.04 mole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for 2 hr and heated at reflux for 5 hr. The reaction mixture was filtered hot to remove some crystalline sulfur and the filtrate solidified on cooling to give 8.3 g of crude product. After 5 recrystallizations from methyl ethyl ketone/methanol with charcoal treatment of the final recrystallization, a crystalline product was obtained, 3.4 g, mp 195°-196° C. After drying at 82° C. under reduced pressure, it was submitted for elemental analysis. heated at reflux for 5 hr The reaction mixture was filtered hot to remove some crystalline sulfur on cooling