1,6-dichlorohexane

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

Procedure: To a stirred mixture of 3.2 parts of a sodium hydride dispersion 70% in 9 parts of N,N-dimethylformamide is added dropwise (slowly), during a 2 hours-period, a mixture of 17.4 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one, 77.5 parts of 1,6-dichlorohexane and 36 parts of N,N-dimethylformamide. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is filtered over hyflo and the N,N-dimethylformamide is evaporated in vacuo. The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet. The residue is dissolved in methylbenzene and the solution is stirred with activated charcoal. The latter is filtered off over hyflo and the filtrate is evaporated, yielding 1-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one as an oily residue. is added dropwise (slowly), during a 2 hours-period The reaction mixture is filtered over hyflo the N,N-dimethylformamide is evaporated in vacuo The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet The residue is dissolved in methylbenzene the solution is stirred with activated charcoal The latter is filtered off over hyflo the filtrate is evaporated

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

Procedure: 6.95 g (0.02 mol) of 5-(3'5'-di-tert.-butyl-4'-hydroxy-phenylethyl)-5-methylhydantoin, 1.4 g (0.01 mol) of potassium carbonate and 1.55 g (0.01 mol) of 1,6-dichlorohexane in 30 ml of dimethylformamide are stirred for 20 hours at 100° C under nitrogen. After cooling, the mixture is added slowly to 120 ml of water with stirring. The precipitated solid is removed by filtration, dried and dissolved in 40 ml of ethanol and decolorized with charcoal. The ethanol solution is filtered and the filtrate added to 400 ml of water with stirring to yield a thick, white suspension which is then filtered. 3,3'-Hexamethylene-bis [5(3",5"-di-tert.-butyl-4"-hydroxyphenylethyl)-5-methylhydantoin] is thus obtained as a white solid of melting point 100°-112° C. (stabiliser No. 22). After cooling The precipitated solid is removed by filtration dried dissolved in 40 ml of ethanol The ethanol solution is filtered the filtrate added to 400 ml of water with stirring to yield a thick, white suspension which is then filtered

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

Procedure: 6.95 g (0.02 mol) of 5-(3'5'-di-tert.-butyl-4'-hydroxy-phenylethyl)-5-methylhydantoin, 1.4 g (0.01 mol) of potassium carbonate and 1.55 g (0.01 mol) of 1,6-dichlorohexane in 30 ml of dimethylformamide are stirred for 20 hours at 100° C under nitrogen. After cooling, the mixture is added slowly to 120 ml of water with stirring. The precipitated solid is removed by filtration, dried and dissolved in 40 ml of ethanol and decolorized with charcoal. The ethanol solution is filtered and the filtrate added to 400 ml of water with stirring to yield a thick, white suspension which is then filtered. 3,3'-Hexamethylene-bis [5(3",5"-di-tert.-butyl-4"-hydroxyphenylethyl)-5-methylhydantoin] is thus obtained as a white solid of melting point 100°-112° C. (stabiliser No. 22). After cooling The precipitated solid is removed by filtration dried dissolved in 40 ml of ethanol The ethanol solution is filtered the filtrate added to 400 ml of water with stirring to yield a thick, white suspension which is then filtered

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

Procedure: To a stirred mixture of 3.2 parts of a sodium hydride dispersion 70% in 9 parts of N,N-dimethylformamide is added dropwise (slowly), during a 2 hours-period, a mixture of 17.4 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one, 77.5 parts of 1,6-dichlorohexane and 36 parts of N,N-dimethylformamide. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is filtered over hyflo and the N,N-dimethylformamide is evaporated in vacuo. The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet. The residue is dissolved in methylbenzene and the solution is stirred with activated charcoal. The latter is filtered off over hyflo and the filtrate is evaporated, yielding 1-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one as an oily residue. is added dropwise (slowly), during a 2 hours-period The reaction mixture is filtered over hyflo the N,N-dimethylformamide is evaporated in vacuo The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet The residue is dissolved in methylbenzene the solution is stirred with activated charcoal The latter is filtered off over hyflo the filtrate is evaporated

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

Procedure: To a stirred mixture of 3.2 parts of a sodium hydride dispersion 70% in 9 parts of N,N-dimethylformamide is added dropwise (slowly), during a 2 hours-period, a mixture of 17.4 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one, 77.5 parts of 1,6-dichlorohexane and 36 parts of N,N-dimethylformamide. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is filtered over hyflo and the N,N-dimethylformamide is evaporated in vacuo. The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet. The residue is dissolved in methylbenzene and the solution is stirred with activated charcoal. The latter is filtered off over hyflo and the filtrate is evaporated, yielding 1-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one as an oily residue. is added dropwise (slowly), during a 2 hours-period The reaction mixture is filtered over hyflo the N,N-dimethylformamide is evaporated in vacuo The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet The residue is dissolved in methylbenzene the solution is stirred with activated charcoal The latter is filtered off over hyflo the filtrate is evaporated

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

Procedure: 106.1 g (1.0 mol) of sodium acetylcyanamide and 77.5 g (0.5 mol) of 1,6-dichlorohexane are reacted in 750 ml of dimethylformamide at 146°-147° C. for 8 hours, the mixture is then filtered with suction and the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo. 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5), are obtained. The yield of pure substance is 58.8 g (46.9% of theory) and the product has a melting point of 59°-61° C. the mixture is then filtered with suction the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5) are obtained

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

Procedure: 106.1 g (1.0 mol) of sodium acetylcyanamide and 77.5 g (0.5 mol) of 1,6-dichlorohexane are reacted in 750 ml of dimethylformamide at 146°-147° C. for 8 hours, the mixture is then filtered with suction and the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo. 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5), are obtained. The yield of pure substance is 58.8 g (46.9% of theory) and the product has a melting point of 59°-61° C. the mixture is then filtered with suction the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5) are obtained

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

Procedure: 106.1 g (1.0 mol) of sodium acetylcyanamide and 77.5 g (0.5 mol) of 1,6-dichlorohexane are reacted in 750 ml of dimethylformamide at 146°-147° C. for 8 hours, the mixture is then filtered with suction and the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo. 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5), are obtained. The yield of pure substance is 58.8 g (46.9% of theory) and the product has a melting point of 59°-61° C. the mixture is then filtered with suction the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5) are obtained

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

Procedure: 106.1 g (1.0 mol) of sodium acetylcyanamide and 77.5 g (0.5 mol) of 1,6-dichlorohexane are reacted in 750 ml of dimethylformamide at 146°-147° C. for 8 hours, the mixture is then filtered with suction and the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo. 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5), are obtained. The yield of pure substance is 58.8 g (46.9% of theory) and the product has a melting point of 59°-61° C. the mixture is then filtered with suction the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5) are obtained

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

Procedure: 128 g of 5,5-dimethyl-hydantoin (1.0 mol), 69 g of anhydrous potassium carbonate (0.5 mol) and 775 g of 1,6-dichlorohexane are reacted at 132°-150° C internal temperature (external temperature 160° C) and the resulting water of reaction is removed continuously by azeotropic circulatory distillation. After 6 hours 25 minutes, the reaction is complete and the reaction mixture is filtered hot to remove the potassium chloride formed. The filtrate is concentrated on a rotary evaporator and dried to constant weight at 100° C and 10-1 mm Hg. is removed continuously by azeotropic circulatory distillation the reaction mixture is filtered hot to remove the potassium chloride formed The filtrate is concentrated on a rotary evaporator dried to constant weight at 100° C

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

Procedure: To a stirred mixture of 3.2 parts of a sodium hydride dispersion 70% in 9 parts of N,N-dimethylformamide is added dropwise (slowly), during a 2 hours-period, a mixture of 17.4 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one, 77.5 parts of 1,6-dichlorohexane and 36 parts of N,N-dimethylformamide. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is filtered over hyflo and the N,N-dimethylformamide is evaporated in vacuo. The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet. The residue is dissolved in methylbenzene and the solution is stirred with activated charcoal. The latter is filtered off over hyflo and the filtrate is evaporated, yielding 1-(6-chlorohexyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one as an oily residue. is added dropwise (slowly), during a 2 hours-period The reaction mixture is filtered over hyflo the N,N-dimethylformamide is evaporated in vacuo The excess of 1,6-dichlorohexane is distilled off in an oil-bath with water-jet The residue is dissolved in methylbenzene the solution is stirred with activated charcoal The latter is filtered off over hyflo the filtrate is evaporated

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

Procedure: The above mentioned compound was prepared analogously to the procedure described in J. Het. Chem. 18, 85 (1981) from 1-( -phenylvinyl)-2,3-dihydro-1H-benzimidazol-2-one and 1,6-dichloro hexane. The protecting group was then removed by acid hydrolysis with hydrochloric acid following the above procedure. M.p. 80°-84° C. was prepared analogously to the procedure The protecting group was then removed by acid hydrolysis with hydrochloric acid following the above procedure