N'-phenylmethoxyethane-1,2-diamine;dihydrochloride

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

Procedure: 400 ml. of water are added to 143.5 g. of N-(benzyloxy)ethylenediamine dihydrochloride. 207.0 g. of potassium carbonate are gradually added carefully to this suspension. Thereafter, 200 ml. of toluene and then, slowly, 145.7 g. of 2,6-dichlorophenylimidocarbonyl chloride in 100 ml. of toluene are added dropwise in the course of 45 minutes, while stirring vigorously. After 15 minutes, a product begins to separate out. The mixture is further stirred overnight and then poured onto 1 liter of n-hexane. The precipitate is filtered off and washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114°-117°, is obtained. to separate out The mixture is further stirred overnight poured onto 1 liter of n-hexane The precipitate is filtered off washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114°-117° is obtained

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

Procedure: 400 ml. of water are added to 143.5 g. of N-(benzyloxy)ethylenediamine dihydrochloride. 207.0 g. of potassium carbonate are gradually added carefully to this suspension. Thereafter, 200 ml. of toluene and then, slowly, 145.7 g. of 2,6-dichlorophenylimidocarbonyl chloride in 100 ml. of toluene are added dropwise in the course of 45 minutes, while stirring vigorously. After 15 minutes, a product begins to separate out. The mixture is further stirred overnight and then poured onto 1 liter of n-hexane. The precipitate is filtered off and washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114°-117°, is obtained. to separate out The mixture is further stirred overnight poured onto 1 liter of n-hexane The precipitate is filtered off washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114°-117° is obtained

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

Procedure: 400 ml. of water are added to 143.5 g. of N-(benzyloxy)ethylenediamine dihydrochloride. 207.0 g. of potassium carbonate are gradually added carefully to this suspension. Thereafter, 200 ml. of toluene and then, slowly, 145.7 g. of 2,6-dichlorophenylimidocarbonyl chloride in 100 ml. of toluene are added dropwise in the course of 45 minutes, while stirring vigorously. After 15 minutes, a product begins to separate out. The mixture is further stirred overnight and then poured onto 1 liter of n-hexane. The precipitate is filtered off and washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114°-117°, is obtained. to separate out The mixture is further stirred overnight poured onto 1 liter of n-hexane The precipitate is filtered off washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114°-117° is obtained

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

Procedure: A suspension of 21.6 g of N-(benzyloxy)ethylenediamine dihydrochloride in 250 ml of toluene is treated with 18.8 g of o-tolylimidocarbonyl chloride, 3.4 g of tetra-n-butylammonium hydrogen sulfate and, while stirring vigorously, dropwise with 80 ml of 28 percent sodium hydroxide. In so doing, the temperature rises to 52°. The mixture is stirred overnight and diluted with ether. The organic phase is separated, washed with water and extracted three times with 3 N sulfuric acid. The aqueous-acidic phase is made alkaline with concentrated sodium hydroxide and extracted with ether. The ethereal solution is dried and evaporated in vacuo. There is obtained 1-(benzyloxy)-2-[(o-tolyl)imino]imidazolidine as a viscous oil which is used directly in the next step. rises to 52° The organic phase is separated washed with water extracted three times with 3 N sulfuric acid extracted with ether The ethereal solution is dried evaporated in vacuo

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

Procedure: 400 ml. of water are added to 143.5 g. of N-(benzyloxy)ethylenediamine dihydrochloride. 270.0 g. of potassium carbonate are gradually added carefully to this suspension. Thereafter, 200 ml. of toluene and then, slowly, 145.7 g. of 2,6 -dichlorophenylimidocarbonyl chloride in 100 ml. of toluene are added dropwise in the course of 45 minutes, while stirring vigorously. After 15 minutes, a product begins to separate out. The mixture is further stirred overnight and then poured onto 1 liter of n-hexane. The precipitate is filtered off and washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114-117°, is obtained. to separate out The mixture is further stirred overnight poured onto 1 liter of n-hexane The precipitate is filtered off washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114-117° is obtained

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

Procedure: 400 ml. of water are added to 143.5 g. of N-(benzyloxy)ethylenediamine dihydrochloride. 207.0 g. of potassium carbonate are gradually added carefully to this suspension. Thereafter, 200 ml. of toluene and then, slowly, 145.7 g. of 2,6-dichlorophenylimidocarbonyl chloride in 100 ml. of toluene are added dropwise in the course of 45 minutes, while stirring vigorously. After 15 minutes, a product begins to separate out. The mixture is further stirred overnight and then poured onto 1 liter of n-hexane. The precipitate is filtered off and washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114°-117°, is obtained. to separate out The mixture is further stirred overnight poured onto 1 liter of n-hexane The precipitate is filtered off washed with water and with n-hexane, whereupon 1-benzyloxy-2-[(2,6-dichlorophenyl)imino]imidazolidine, m.p. 114°-117° is obtained