2,3,4,5,6-pentachlorobenzonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 18.0 gms. pentachlorobenzonitrile and 200 ml concentrated sulfuric acid (97 weight % H2SO4) was heated to 145° C. over a period of approximately 40 min. Complete dissolution of the pentachlorobenzonitrile was observed to occur at 130° C. thereby giving a pale straw solution. When cool, the reaction mixture was poured onto ice and the white solid thereby formed was isolated by filtration. In this manner there was formed 18.0 gms. (94% yield) pentachlorobenzamide. Identity of the product was established with the aid of both analytical and spectral data. A mixture of 18.0 gms to occur at 130° C. thereby giving a pale straw solution When cool the reaction mixture was poured onto ice the white solid thereby formed was isolated by filtration In this manner there was formed 18.0 gms

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

Procedure: In a preferred embodiment of the invention, pentachlorobenzonitrile is interacted with a molar excess of sulfuric acid having at least 75% by weight H2SO4 at a temperature of between about 130° and 160° C. for about fifteen (15) to ninety (90) minutes. The reaction mixture is then cooled and diluted with water to form a solid pentachlorobenzamide precipitate. The resultant pentachlorobenzamide is recovered in yields on the average of above about 90%. at a temperature of between about 130° and 160° C. The reaction mixture is then cooled

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

Procedure: In a preferred embodiment of the invention, pentachlorobenzonitrile is interacted with a molar excess of sulfuric acid having at least 75% by weight H2SO4 at a temperature of between about 130° and 160° C. for about fifteen (15) to ninety (90) minutes. The reaction mixture is then cooled and diluted with water to form a solid pentachlorobenzamide precipitate. The resultant pentachlorobenzamide is recovered in yields on the average of above about 90%. at a temperature of between about 130° and 160° C. The reaction mixture is then cooled

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

Procedure: 27.6 g of pentachlorobenzonitrile and 32 g of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid 2-aminoethylamide are reacted with 11 g of triethylamine in 200 g of N-methylpyrrolidone for 7 hours at 100° C., after which 500 g of water and 400 g of toluene are added, and the toluene phase is separated off while still hot and evaporated down under reduced pressure. The residue is boiled with 0.15 l of ethanol, and the mixture is left to stand overnight at room temperature. The precipitate is then filtered off under suction and dried. After recrystallization from toluene, the product melts at 173°-175° C. the toluene phase is separated off while still hot and evaporated down under reduced pressure the mixture is left The precipitate is then filtered off under suction dried After recrystallization from toluene

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

Procedure: 27.6 g of pentachlorobenzonitrile and 32 g of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid 2-aminoethylamide are reacted with 11 g of triethylamine in 200 g of N-methylpyrrolidone for 7 hours at 100° C., after which 500 g of water and 400 g of toluene are added, and the toluene phase is separated off while still hot and evaporated down under reduced pressure. The residue is boiled with 0.15 l of ethanol, and the mixture is left to stand overnight at room temperature. The precipitate is then filtered off under suction and dried. After recrystallization from toluene, the product melts at 173°-175° C. the toluene phase is separated off while still hot and evaporated down under reduced pressure the mixture is left The precipitate is then filtered off under suction dried After recrystallization from toluene

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

Procedure: 55 g of pentachlorobenzonitrile are introduced into 300 g of ethylenediamine at room temperature in such a way that the temperature does not exceed 30° C. The mixture is then stirred for a further half an hour at room temperature, after which 0.75 l of ice water is slowly added and stirring is continued for 15 minutes. The precipitate is filtered off under suction, washed with water and dried to give 55 g of product which, when recrystallized from toluene with the addition of active carbon, has a melting point of 140°-144° C. does not exceed 30° C stirring The precipitate is filtered off under suction washed with water dried

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

Procedure: To solution of 34.4 grams of pentachlorobenzonitrile in tetrahydrofuran was added a mixture of 8.0 grams ethylene glycol, 8.0 grams of a 50% sodium hydride-mineral oil dispersion and 250 ml tetrahydrofuran. The resulting reaction mixture was heated at reflux for one hour and then poured into a large volume of water. Filtration afforded an almost colorless solid which was dissolved in tetrahydrofuran. Treatment with magnesium sulfate followed by filtration and removal of the solvent gave rise to beta-hydroxyethoxy-tetrachlorobenzonitrile. This material is identical basis both nmr and infrared spectral data to the product formed from the reaction of tetrachlorocyanophenol with ethylene oxide as set forth below. The resulting reaction mixture was heated at reflux for one hour Filtration afforded an almost colorless solid which Treatment with magnesium sulfate followed by filtration and removal of the solvent