cyclohexyl thiohypochlorite

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Similarly, repeating the above procedure but replacing the benzenesulfenyl chloride as used therein with an equal molar proportion of each of decanesulfenyl chloride (prepared by chlorination of decanedisulfide according to the method of Douglass, supra.), 1,2-dichlorovinylsulfenyl chloride, 2-naphthalenesulfenyl chloride, cyclohexanesulfenyl chloride (prepared by chlorination of cyclohexanedisulfide, according to the method of Douglass, supra.) and α-toluenesulfenyl chloride, respectively, there is obtained:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2.6 grams of cyclohexyl chlorosulfide (0.0172 mole) prepared as in Example 1 is added slowly to a stirred solution containing 5.4 grams (0.0163 mole) of N-cyclohexyl-5-chlorobenzothiazole-2-sulfonamide, and 2 grams of triethylamine (0.0178 mole) in 150 ml anhydrous dimethylformamide. The temperature is maintained between about 15° and 20° C. After stirring, 100 ml of chloroform is added and the reaction mixture is poured into 2 liters of ice water, and treated as in Example 5. is added slowly to a stirred solution The temperature is maintained between about 15° and 20° C treated as in Example 5

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7.8 grams (0.0517 mole) of cyclohexyl chlorosulfide prepared as in Example 1 is added over a 60-minute period to a stirred solution of 12 grams (0.0495 mole) of N-ethyl benzothiazole-2-sulfonamide, 5.5 grams of triethylamine (0.0495 mole) in 200 ml anhydrous dimethylformamide and 200 ml chloroform. The temperature is maintained between about 15° and 20° C. The reaction mixture is poured into 2 liters of ice water. The solvent layer is well washed, dehydrated with anhydrous sodium sulfate and any remaining solvent is removed by vacuum distillation. The temperature is maintained between about 15° and 20° C The solvent layer is well washed any remaining solvent is removed by vacuum distillation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: NH3 gas was passed into 80.4 g of trimethylchlorosilane in 500 ml of dry toluene at 50° to 60° C. to saturation. 59.1 g of benzimidazole were then added and the mixture was boiled for 10 hours under reflux. To remove excess ammonia, 250 ml of toluene were distilled off in vacuo, and 0.5 mol of cyclohexylsulphenyl chloride in 500 ml of pentane was then added dropwise. The mixture was subsequently stirred for 4 hours and filtered, and the solvent was removed in vacuo. 99 g of 1-cyclohexylthiobenzimidazole were obtained as a red-brown oil. under reflux To remove excess ammonia, 250 ml of toluene was then added dropwise filtered the solvent was removed in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: NH3 gas was passed into 80.4 g of trimethylchlorosilane in 500 ml of dry toluene at 50° to 60° C. to saturation. 59.1 g of benzimidazole were then added and the mixture was boiled for 10 hours under reflux. To remove excess ammonia, 250 ml of toluene were distilled off in vacuo, and 0.5 mol of cyclohexylsulphenyl chloride in 500 ml of pentane was then added dropwise. The mixture was subsequently stirred for 4 hours and filtered, and the solvent was removed in vacuo. 99 g of 1-cyclohexylthiobenzimidazole were obtained as a red-brown oil. under reflux To remove excess ammonia, 250 ml of toluene was then added dropwise filtered the solvent was removed in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In like manner a mixture comprising 120 grams (2.0 moles) of anhydrous acetic acid and 314 grams (4.3 mole) of n-octylamine along with 200 cc. of xylene is placed in a 1 liter flask equipped with a Dean-Stark water trap. The flask is then heated to reflux and maintained thereat for a period of 3 hours, the water of condensation which is formed during the reaction being continuously removed from the system. At the end of the 3-hour period, the temperature of the flask is increased until the xylene solvent has been distilled off. Upon recovery of the solvent, the reaction mixture is then allowed to cool to room temperature and transferred to a separate flask. The N,N'-dioctylacetamidine which is prepared thusly is then placed in a flask along with triethylamine and a benzene solvent following which the flask is then cooled to a temperature of 0° C. Upon reaching this reduced temperature, the mixture is treated by slowly adding dropwise an equimolar amount of cyclohexanesulfenyl chloride, the temperature of the solution being maintained in a range of from 0° to 10° C. Upon completion of the addition of the cyclohexanesulfenyl chloride which is accompanied by continuous stirring, the mixture is allowed to return to room temperature while maintaining the stirring thereof. At the end of a 1-hour period, the solid which is formed is washed with benzene and air dried for a period of 24 hours. The solution is then washed with water, dried over magnesium sulfate and the benzene solvent is removed by vacuum. Upon further standing, the desired product comprising N,N'-dioctyl-N-cyclohexylthioacetamidine will crystallize out and may be then recrystallized from an isopropyl-ethyl acetate solution. The flask is then heated to reflux maintained is formed during the reaction being continuously removed from the system At the end of the 3-hour period, the temperature of the flask is increased until the xylene solvent has been distilled off transferred to a separate flask the mixture is treated the temperature of the solution being maintained in a range of from 0° to 10° C to return to room temperature while maintaining the stirring thereof At the end of a 1-hour period, the solid which is formed is washed with benzene and air dried for a period of 24 hours The solution is then washed with water dried over magnesium sulfate the benzene solvent is removed by vacuum will crystallize out may be then recrystallized from an isopropyl-ethyl acetate solution

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The N,N'-diphenylacetamidine which is prepared according to the above paragraph is then placed in a flask along with an acid scavenger comprising triethylamine using dimethylformamide as a solvent. The mixture is cooled to a temperature of 0° C. and maintained thereat while an equimolar amount of cyclohexanesulfenyl chloride is slowly added thereto dropwise. The temperature of the reaction will range from about 0° to about 10° C. with continuous stirring. Following the completion of the addition of the cyclohexanesulfenyl chloride, the reaction mixture is stirred for an additional period of 1 hour while allowing the temperature of the solution to reach room temperature. Following this, water is added and the organic layer which separates out is thereafter washed several times with water, dried over magnesium sulfate and subjected to vacuum to remove the dimethylformamide solvent. The resulting material will slowly crystallize and the crystals comprising N,N'-diphenyl-N-cyclohexylthioacetamidine will be recovered by filtration. is then placed in a flask along with an acid scavenger maintained The temperature of the reaction will range from about 0° to about 10° C. with continuous stirring to reach room temperature is added the organic layer which separates out is thereafter washed several times with water dried over magnesium sulfate to remove the dimethylformamide solvent The resulting material will slowly crystallize will be recovered by filtration

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Similarly, repeating the above procedure but replacing the benzenesulfenyl chloride as used therein with an equal molar proportion of each of decanesulfenyl chloride (prepared by chlorination of decanedisulfide according to the method of Douglass, supra.), 1,2-dichlorovinylsulfenyl chloride, 2-naphthalenesulfenyl chloride, cyclohexanesulfenyl chloride (prepared by chlorination of cyclohexanedisulfide, according to the method of Douglass, supra.) and α-toluenesulfenyl chloride, respectively, there is obtained:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2.6 grams of cyclohexyl chlorosulfide (0.0172 mole) prepared as in Example 1 is added slowly to a stirred solution containing 5.4 grams (0.0163 mole) of N-cyclohexyl-5-chlorobenzothiazole-2-sulfonamide, and 2 grams of triethylamine (0.0178 mole) in 150 ml anhydrous dimethylformamide. The temperature is maintained between about 15° and 20° C. After stirring, 100 ml of chloroform is added and the reaction mixture is poured into 2 liters of ice water, and treated as in Example 5. is added slowly to a stirred solution The temperature is maintained between about 15° and 20° C treated as in Example 5

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7.8 grams (0.0517 mole) of cyclohexyl chlorosulfide prepared as in Example 1 is added over a 60-minute period to a stirred solution of 12 grams (0.0495 mole) of N-ethyl benzothiazole-2-sulfonamide, 5.5 grams of triethylamine (0.0495 mole) in 200 ml anhydrous dimethylformamide and 200 ml chloroform. The temperature is maintained between about 15° and 20° C. The reaction mixture is poured into 2 liters of ice water. The solvent layer is well washed, dehydrated with anhydrous sodium sulfate and any remaining solvent is removed by vacuum distillation. The temperature is maintained between about 15° and 20° C The solvent layer is well washed any remaining solvent is removed by vacuum distillation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: NH3 gas was passed into 80.4 g of trimethylchlorosilane in 500 ml of dry toluene at 50° to 60° C. to saturation. 59.1 g of benzimidazole were then added and the mixture was boiled for 10 hours under reflux. To remove excess ammonia, 250 ml of toluene were distilled off in vacuo, and 0.5 mol of cyclohexylsulphenyl chloride in 500 ml of pentane was then added dropwise. The mixture was subsequently stirred for 4 hours and filtered, and the solvent was removed in vacuo. 99 g of 1-cyclohexylthiobenzimidazole were obtained as a red-brown oil. under reflux To remove excess ammonia, 250 ml of toluene was then added dropwise filtered the solvent was removed in vacuo