4-CYCLOHEXYL-3-THIOSEMICARBAZIDE

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 from a mixture of 4-cyclohexyl-3-thiosemicarbazide (100 mg, 0.577 mmol) and 2-pyridinecarboxaldehyde (55 μL, 0.577 mmol) similar to Example 3 and isolated as a white solid (40 mg, 26%). 1H NMR (CDCl3): 9.16 (s, 1H), 8.65-8.63 (m, 1H), 7.87-7.85 (m, 2H), 7.78-7.73 (m, 1H), 7.38 (d, J=7.2 Hz, 1H), 7.34-7.27 (m, 1H), 4.344.27 (m, 1H), 2.18-2.12 (m, 2H), 1.82-1.75 (m, 2H), 1.50-1.22 (m, 6H).

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

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

Procedure: A mixture of 34.7 g (0.2 mole) of 4-cyclohexyl-3-thiosemicarbazide and 32.9 g (0.2 mole) of ethyl 2-chloroacetoacetate in 350 mL of absolute ethanol was stirred under nitrogen atmosphere at ambient temperature for 2 hr, treated with 100 mL of 2N ethanolic hydrogen chloride and heated at reflux for 2 hr. The hot reaction mixture was filtered to remove an amorphous solid. The product persistently crystallized in the filter. The product was recrystallized from acetone and recovered by decating off hot acetone solvent and washing the residue with cold acetone to give 27 g of large, off-white crystals, mp 178-182° C. heated at reflux for 2 hr The hot reaction mixture was filtered to remove an amorphous solid The product persistently crystallized in the filter The product was recrystallized from acetone recovered washing the residue with cold acetone to give 27 g of large, off-white crystals, mp 178-182° C.

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

Procedure: A mixture of 34.7 g (0.2 mole) of 4-cyclohexyl-3-thiosemicarbazide and 32.9 g (0.2 mole) of ethyl 2-chloroacetoacetate in 350 mL of absolute ethanol was stirred under nitrogen atmosphere at ambient temperature for 2 hr, treated with 100 mL of 2N ethanolic hydrogen chloride and heated at reflux for 2 hr. The hot reaction mixture was filtered to remove an amorphous solid. The product persistently crystallized in the filter. The product was recrystallized from acetone and recovered by decating off hot acetone solvent and washing the residue with cold acetone to give 27 g of large, off-white crystals, mp 178°-182° C. heated at reflux for 2 hr The hot reaction mixture was filtered to remove an amorphous solid The product persistently crystallized in the filter The product was recrystallized from acetone recovered washing the residue with cold acetone to give 27 g of large, off-white crystals, mp 178°-182° C.

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

Procedure: The title compound was prepared from a mixture of 4-cyclohexyl-3-thiosemicarbazide (100 mg, 0.577 mmol) and 2-pyridinecarboxaldehyde (55 μL, 0.577 mmol) similar to Example 3 and isolated as a white solid (40 mg, 26%). 1H NMR (CDCl3): 9.16 (s, 1H), 8.65-8.63 (m, 1H), 7.87-7.85 (m, 2H), 7.78-7.73 (m, 1H), 7.38 (d, J=7.2 Hz, 1H), 7.34-7.27 (m, 1H), 4.344.27 (m, 1H), 2.18-2.12 (m, 2H), 1.82-1.75 (m, 2H), 1.50-1.22 (m, 6H).