1,1-diethoxy-2-isothiocyanatoethane

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

Procedure: To 17.85 g (0.1013 mole) of 5-amino-6-fluoro-2-methylquinoline was added 19.5 g (0.1114 mole) of 2,2-diethoxyethylisothiocyanate and the mixture was heated at 80°-90° C. for 1.5 hours. The residue was slurried in ethanol, separated by filtration, washed with ethanol and then recrystallized from ethanol to provide N-(2,2-diethoxyethyl)-N'-(6-fluoro-2-methylquinolin-5-yl)thiourea, m.p. 189°-191° C. the mixture was heated at 80°-90° C. for 1.5 hours separated by filtration washed with ethanol recrystallized from ethanol

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

Procedure: To 17.85 g (0.1013 mole) of 5-amino-6-fluoro-2-methylquinoline was added 19.5 g (0.1114 mole) of 2,2-diethoxyethylisothiocyanate and the mixture was heated at 80°-90° C. for 1.5 hours. The residue was slurried in ethanol, separated by filtration, washed with ethanol and then recrystallized from ethanol to provide N-(2,2-diethoxyethyl)-N'-(6-fluoro-2-methylquinolin-5-yl)thiourea, m.p. 189°-191° C. the mixture was heated at 80°-90° C. for 1.5 hours separated by filtration washed with ethanol recrystallized from ethanol

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

Procedure: To 17.85 g (0.1013 mole) of 5-amino-6-fluoro-2-methylquinoline was added 19.5 g (0.1114 mole) of 2,2-diethoxyethylisothiocyanate and the mixture was heated at 80°-90° C. for 1.5 hours. The residue was slurried in ethanol, separated by filtration, washed with ethanol and then recrystallized from ethanol to provide N-(2,2-diethoxyethyl)-N'-(6-fluoro-2-methylquinolin-5-yl)thiourea, m.p. 189°-191° C. Analysis: Calculated for C17H22FN3O2S: %C, 58.1; %H, 6.3; %N, 12.1; Found: %C, 58.3; %H, 6.5; %N, 11.9. the mixture was heated at 80°-90° C. for 1.5 hours separated by filtration washed with ethanol recrystallized from ethanol

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

Procedure: A solution of 120 ml of carbon disulfide and 60.6 g of dicyclohexycarbodiimide in 300 ml of tetrahydrofuran is cooled to -8° with an ice/salt mixture. Thereupon, 39.9 g of aminoacetaldehyde diethyl acetal are added dropwise while stirring so that the temperature of the reaction mixture does not exceed -5° (approximately 1 hour). The mixture is then warmed slowly to room temperature while stirring (approximately 2 hours) and left to stand overnight. The resulting precipitate (dicyclohexylthiourea) is then removed by filtration and washed thoroughly with n-hexane. The filtrate is concentrated in a vacuum and the separated dicyclohexylthiourea is again removed by filtration and washed with n-hexane. This procedure is repeated until dicyclohexylthiourea no longer separates upon concentration. Finally, the filtrate is freed completely from solvents. The residue is distilled at 11 Torr (bath temperature 130°-134°), whereby there is obtained 2,2-diethoxyethyl isothiocyanate in the form of a colorless oil; b.p. 100°/11 Torr. does not exceed -5° (approximately 1 hour) while stirring (approximately 2 hours) left The resulting precipitate (dicyclohexylthiourea) is then removed by filtration washed thoroughly with n-hexane The filtrate is concentrated in a vacuum the separated dicyclohexylthiourea is again removed by filtration washed with n-hexane no longer separates upon concentration The residue is distilled at 11 Torr (bath temperature 130°-134°)