N,2,6-trimethylaniline

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

Procedure: To 40.5 g. (0.315 mole) of N-methyl-2,6-dimethylaniline is added 0.4 moles of ethereal HCl and 200 ml. of m-cresol. The mixture is then stirred and heated on a steam bath to drive off the ether and excess hydrogen chloride. To the resultant mixture is then added 13.3 g. (0.315 mole) of cyanamide then heated for 2 hours on a steam bath. The reaction mixture is then cooled, added to 150 ml. of conc. sodium hydroxide solution, cooled and extracted with 2 liters of ether. The ether layer is washed with 2 × 1 liter of water, dried over sodium sulfate, charcoaled and evaporated. The residue is triturated with hexane and the precipitate is filtered off and washed with ether and dried to obtain 1-(2,6-dimethylphenyl)-1-methylguanidine. heated on a steam bath The reaction mixture is then cooled added to 150 ml extracted with 2 liters of ether The ether layer is washed with 2 × 1 liter of water dried over sodium sulfate evaporated The residue is triturated with hexane the precipitate is filtered off washed with ether dried

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

Procedure: To 40.5 g. (0.315 mole) of N-methyl-2,6-dimethylaniline is added 0.4 moles of ethereal HCl and 200 ml. of m-cresol. The mixture is then stirred and heated on a steam bath to drive off the ether and excess hydrogen chloride. To the resultant mixture is then added 13.3 g. (0.315 mole) of cyanamide then heated for 2 hours on a steam bath. The reaction mixture is then cooled, added to 150 ml. of conc. sodium hydroxide solution, cooled and extracted with 2 liters of ether. The ether layer is washed with 2 × 1 liter of water, dried over sodium sulfate, charcoaled and evaporated. The residue is triturated with hexane and the precipitate is filtered off and washed with ether and dried to obtain 1-(2,6-dimethylphenyl)-1-methylguanidine. heated on a steam bath The reaction mixture is then cooled added to 150 ml extracted with 2 liters of ether The ether layer is washed with 2 × 1 liter of water dried over sodium sulfate evaporated The residue is triturated with hexane the precipitate is filtered off washed with ether dried

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

Procedure: To 40.5 g. (0.315 mole) of N-methyl-2,6-dimethylaniline is added 0.4 moles of ethereal HCl and 200 ml. of m-cresol. The mixture is then stirred and heated on a steam bath to drive off the ether and excess hydrogen chloride. To the resultant mixture is then added 13.3 g. (0.315 mole) of cyanamide then heated for 2 hours on a steam bath. The reaction mixture is then cooled, added to 150 ml. of conc. sodium hydroxide solution, cooled and extracted with 2 liters of ether. The ether layer is washed with 2×1 liter of water, dried over sodium sulfate, charcoaled and evaporated. The residue is triturated with hexane and the precipitate is filtered off and washed with ether and dried to obtain 1-(2,6-dimethylphenyl)-1-methylguanidine. heated on a steam bath The reaction mixture is then cooled added to 150 ml extracted with 2 liters of ether The ether layer is washed with 2×1 liter of water dried over sodium sulfate evaporated The residue is triturated with hexane the precipitate is filtered off washed with ether dried

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

Procedure: In a 500 ml four-neck flask, 41.0 parts of a sulfofluoran compound of the following chemical formula (5), 312 parts of methanol, 6.79 parts of N-methyl-2,6-xylidine and 6.13 parts of N-methyl-o-toluidine were put and refluxed for 30 hours. The reaction solution was filtered at 60° C. to remove insoluble substances therefrom. Then, the solvent was removed under a reduced pressure, until the amount of the reaction solution reached about 70 ml. The reaction solution was poured into 200 parts of 6% hydrochloric acid. Then, 600 parts of water was added thereto and the mixture was stirred at room temperature for 30 minutes. Then, a wet cake was obtained by filtration. The wet cake was suspended in 100 parts of water and stirred at 60° C. for 2 hours. Then, the wet cake was obtained again by filtration, washed with hot water at 60° C. and then dried, thereby obtaining the xanthene-based dye A represented by the following chemical formula (6). refluxed for 30 hours The reaction solution was filtered at 60° C. to remove insoluble substances Then, the solvent was removed under a reduced pressure, until the amount of the reaction solution The reaction solution was poured into 200 parts of 6% hydrochloric acid Then, 600 parts of water was added Then, a wet cake was obtained by filtration stirred at 60° C. for 2 hours Then, the wet cake was obtained again by filtration washed with hot water at 60° C. dried

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

Procedure: In a 500 ml four-neck flask, 41.0 parts of a sulfofluoran compound of the following chemical formula (5), 312 parts of methanol, 6.79 parts of N-methyl-2,6-xylidine and 6.13 parts of N-methyl-o-toluidine were put and refluxed for 30 hours. The reaction solution was filtered at 60° C. to remove insoluble substances therefrom. Then, the solvent was removed under a reduced pressure, until the amount of the reaction solution reached about 70 ml. The reaction solution was poured into 200 parts of 6% hydrochloric acid. Then, 600 parts of water was added thereto and the mixture was stirred at room temperature for 30 minutes. Then, a wet cake was obtained by filtration. The wet cake was suspended in 100 parts of water and stirred at 60° C. for 2 hours. Then, the wet cake was obtained again by filtration, washed with hot water at 60° C. and then dried, thereby obtaining the xanthene-based dye A represented by the following chemical formula (6). refluxed for 30 hours The reaction solution was filtered at 60° C. to remove insoluble substances Then, the solvent was removed under a reduced pressure, until the amount of the reaction solution The reaction solution was poured into 200 parts of 6% hydrochloric acid Then, 600 parts of water was added Then, a wet cake was obtained by filtration stirred at 60° C. for 2 hours Then, the wet cake was obtained again by filtration washed with hot water at 60° C. dried

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

Procedure: To 40.5 g. (0.315 mole) of N-methyl-2,6-dimethylaniline is added 0.4 moles of ethereal HCl and 200 ml. of m-cresol. The mixture is then stirred and heated on a steam bath to drive off the ether and excess hydrogen chloride. To the resultant mixture is then added 13.3 g. (0.315 mole) of cyanamide then heated for 2 hours on a steam bath. The reaction mixture is then cooled, added to 150 ml. of conc. sodium hydroxide solution, cooled and extracted with 2 liters of ether. The ether layer is washed with 2 × 1 liter of water, dried over sodium sulfate, charcoaled and evaporated. The residue is triturated with hexane and the precipitate is filtered off and washed with ether and dried to obtain 1-(2,6-dimethylphenyl)-1-methylguanidine. heated on a steam bath The reaction mixture is then cooled added to 150 ml extracted with 2 liters of ether The ether layer is washed with 2 × 1 liter of water dried over sodium sulfate evaporated The residue is triturated with hexane the precipitate is filtered off washed with ether dried

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 14.0 g (0.25 mol) of acrolein is added dropwise at 25° to 30° C. to 23.3 g (0.15 mol) of N-(3-penten-2-yl)-morpholine. The mixture obtained is stirred for 15 hours at 25° C. and subsequently, for further 15 hours at 50° C. Then the mixture is transferred into an autoclave and after addition of 400 ml of a 40% by weight aqueous solution of methylamine and 10.0 g of palladium coal (5%), the whole is heated under a nitrogen pressure of 50 bar for 5 hours at 280° to 290° C. Subsequently the catalyst is separated off by filtration and washed with ether. The filtrate is several times extracted with ether, the combined extracts are dried over magnesium sulphate and the ether is distilled off. Then water is added to the residue and the whole is acidified by addition of hydrochloric acid. The acid solution obtained is extracted with ether and the extract is discarded. Now sodium bicarbonate is added to the acid solution until the mixture shows alkaline reaction and the whole is again extracted with ether. The extract is dried over sodium sulphate and the ether is distilled off. N-methyl-2,6-dimethylaniline is obtained by distillation of the residue at 0.1 Torr. The mixture obtained subsequently, for further 15 hours at 50° C the whole is heated under a nitrogen pressure of 50 bar for 5 hours at 280° to 290° C Subsequently the catalyst is separated off by filtration washed with ether extracted with ether the combined extracts are dried over magnesium sulphate the ether is distilled off Then water is added to the residue the whole is acidified by addition of hydrochloric acid The acid solution obtained is extracted with ether Now sodium bicarbonate is added to the acid solution until the mixture reaction the whole is again extracted with ether The extract is dried over sodium sulphate the ether is distilled off