1-(furan-2-yl)-N,N-dimethylmethanamine

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

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

Procedure: N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg). the mixture left extracted with ethyl acetate The combined extracts were purified by preparative layer chromatography

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

Procedure: Methyl 1-methyl-N-[(methylsulphonyl)acetyl]-2-(phenylmethylene)hydrazinecarboximidothioate (1.05 g) and 5-[[2-aminoethyl)thio]methyl]-N,N-dimethylfuranmethanamine (0.85 g)in acetonitrile (3 ml) were heated on a steam bath at atmospheric pressure for 5 minutes then under water vacuum for 10 minutes. The oily residue was dissolved in acetonitrile (3 ml) and the solution re-evaporated under water vacuum. The oily residue was dissolved in 2N hydrochloric acid (3 ml) and 5N hydrochloric acid (4 ml) added to the solution. The solution was heated on a steam bath for 15 minutes and after cooling to room temperature, water (10 ml) was added and the oily suspension extracted with ethyl acetate. The aqueous phase was basified with sodium carbonate and the oily suspension extracted with ethyl acetate to yield an oil (0.84 g). This was chromatographed (using solvent system D) to give the title compound (0.78 g) as an oil. T.l.c. System D, Rf 0.5. the solution re-evaporated under water vacuum The oily residue was dissolved in 2N hydrochloric acid (3 ml) 5N hydrochloric acid (4 ml) added to the solution The solution was heated on a steam bath for 15 minutes water (10 ml) was added the oily suspension extracted with ethyl acetate the oily suspension extracted with ethyl acetate

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

Procedure: N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg). the mixture left extracted with ethyl acetate The combined extracts were purified by preparative layer chromatography

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

Procedure: N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg). the mixture left extracted with ethyl acetate The combined extracts were purified by preparative layer chromatography

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

Procedure: N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg). the mixture left extracted with ethyl acetate The combined extracts were purified by preparative layer chromatography

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

Procedure: N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg). the mixture left extracted with ethyl acetate The combined extracts were purified by preparative layer chromatography

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

Procedure: N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg). the mixture left extracted with ethyl acetate The combined extracts were purified by preparative layer chromatography

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

Procedure: Methyl 1-methyl-N-[(methylsulphonyl)acetyl]-2-(phenylmethylene)hydrazinecarboximidothioate (1.05 g) and 5-[[2-aminoethyl)thio]methyl]-N,N-dimethylfuranmethanamine (0.85 g)in acetonitrile (3 ml) were heated on a steam bath at atmospheric pressure for 5 minutes then under water vacuum for 10 minutes. The oily residue was dissolved in acetonitrile (3 ml) and the solution re-evaporated under water vacuum. The oily residue was dissolved in 2N hydrochloric acid (3 ml) and 5N hydrochloric acid (4 ml) added to the solution. The solution was heated on a steam bath for 15 minutes and after cooling to room temperature, water (10 ml) was added and the oily suspension extracted with ethyl acetate. The aqueous phase was basified with sodium carbonate and the oily suspension extracted with ethyl acetate to yield an oil (0.84 g). This was chromatographed (using solvent system D) to give the title compound (0.78 g) as an oil. T.l.c. System D, Rf 0.5. the solution re-evaporated under water vacuum The oily residue was dissolved in 2N hydrochloric acid (3 ml) 5N hydrochloric acid (4 ml) added to the solution The solution was heated on a steam bath for 15 minutes water (10 ml) was added the oily suspension extracted with ethyl acetate the oily suspension extracted with ethyl acetate

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

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

Procedure: N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg). the mixture left extracted with ethyl acetate The combined extracts were purified by preparative layer chromatography

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

Procedure: N,N-Dimethyl-2-furanmethanamine (125 mg) was dissolved in glacial acetic acid (1 ml) and paraformaldehyde (30 mg) added. A solution of N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine (354 mg) in concentrated hydrochloric acid (1 ml) and glacial acetic acid (1 ml) was added dropwise and the mixture left to stand at room temperature for 5 days. The solution was diluted with water (30 ml), saturated with potassium carbonate and extracted with ethyl acetate. The combined extracts were purified by preparative layer chromatography to give the title compound as Example 15 (89 mg). the mixture left extracted with ethyl acetate The combined extracts were purified by preparative layer chromatography