morpholin-4-yl morpholine-4-carbodithioate

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

Procedure: In this example, a methylene chloride solution of N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide was prepared by reacting morpholine, dissolved in methylene chloride, sequentially with a NaOCl bleach solution and carbon disulfide in the manner described in U.S. Pat. No. 3,985,743. At the end of the reaction the methylene chloride organic phase was separated from the water phase. The methylene chloride solution was diluted with methylene chloride to a total solids content of 12 percent. 100 volumes of this organic solution containing the N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide was stirred with 100 volumes of hydrochloric acid having a normality of 0.06 N, the HCl being used in amount of 5.8 milliequivalents of acid based on 15.7 grams of solids. The aqueous acid and organic solutions were stirred together for about 15 minutes to a pH of the mixture of 2.7. The acid phase was separated from the organic solution by transferring the mixture to a separating vessel settling the layers, and decanting. The organic solution was then washed twice with 100 volumes of distilled water and separated from the water. The methylene chloride was then flashed off and the dried N-oxydiethylenecarbamyl-N'-oxydiethylenesulfenamide collected. The melting point of the N-oxydiethylenecarbamyl-N'-oxydiethylenesulfenamide was found to be 134.8° C. A sample of N-oxydiethylenecarbamyl-N'-oxydiethylenesulfenamide was aged in an air over at 100° C. for 60 minutes to test for stability. The melting point after aging was determined and found to be 133.0° C., for a ΔT of 1.8, this sample being very stable. When a control run was made without the acid wash, using only water washes, the unaged melting point was found to be 134.4° C. and the aged melting point was found to be 128.4° , for a ΔT of 6.0, which represents a very unstable product with unsatisfactory storage stability and product activity. was separated from the water phase The methylene chloride solution was diluted with methylene chloride to a total solids content of 12 percent 100 volumes of this organic solution containing the N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide The aqueous acid and organic solutions were stirred together for about 15 minutes to a pH of the mixture of 2.7 The acid phase was separated from the organic solution decanting The organic solution was then washed twice with 100 volumes of distilled water separated from the water the dried N-oxydiethylenecarbamyl-N'-oxydiethylenesulfenamide collected to be 134.8° C to be 133.0° C., for a ΔT of 1.8 wash to be 134.4° C. to be 128.4° , for a ΔT of 6.0, which

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide was prepared by reacting about 0.2 mole of morpholine and about 0.2 mole of N-chloromorpholine chloride with 0.2 mole of carbon disulfide in the presence of about 0.2 mole of NaOH and in a medium of water and chloroform. 34.8 grams (0.4 mole) of morpholine was added to 50 milliliters of chloroform and the solution cooled to 0° C. 110 grams of a solution of NaOCl at 13% by weight in water (0.2 mole) was added and the mixture stirred for 10 minutes at a temperature of about 10° C. 15.2 grams (0.2 mole) of carbon disulfide was then added and the mix stirred for 10 minutes at 10°±5° C. The mixture became thick and an additional 50 milliliters of chloroform was added. After 15 minutes of stirring, the mixture was allowed to settle and the non-aqueous phase was separated out. The chloroform was evaporated off under reduced pressure. The pale yellow crystals obtained were slurried in methanol, filtered out and dried. The yield of compound was 45.2 grams, 92% by weight of theoretical. The compound was identified by its IR spectrum, and it had a melting point of 128°-134° C. the mix stirred for 10 minutes at 10°±5° C After 15 minutes of stirring the non-aqueous phase was separated out The chloroform was evaporated off under reduced pressure The pale yellow crystals obtained filtered out dried

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide was prepared by reacting about 0.2 mole of morpholine and about 0.2 mole of N-chloromorpholine chloride with 0.2 mole of carbon disulfide in the presence of about 0.2 mole of NaOH and in a medium of water and chloroform. 34.8 grams (0.4 mole) of morpholine was added to 50 milliliters of chloroform and the solution cooled to 0° C. 110 grams of a solution of NaOCl at 13% by weight in water (0.2 mole) was added and the mixture stirred for 10 minutes at a temperature of about 10° C. 15.2 grams (0.2 mole) of carbon disulfide was then added and the mix stirred for 10 minutes at 10°±5° C. The mixture became thick and an additional 50 milliliters of chloroform was added. After 15 minutes of stirring, the mixture was allowed to settle and the non-aqueous phase was separated out. The chloroform was evaporated off under reduced pressure. The pale yellow crystals obtained were slurried in methanol, filtered out and dried. The yield of compound was 45.2 grams, 92% by weight of theoretical. The compound was identified by its IR spectrum, and it had a melting point of 128°-134° C. the mix stirred for 10 minutes at 10°±5° C After 15 minutes of stirring the non-aqueous phase was separated out The chloroform was evaporated off under reduced pressure The pale yellow crystals obtained filtered out dried

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

Procedure: In this example, a methylene chloride solution of N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide was prepared by reacting morpholine, dissolved in methylene chloride, sequentially with a NaOCl bleach solution and carbon disulfide in the manner described in U.S. Pat. No. 3,985,743. At the end of the reaction the methylene chloride organic phase was separated from the water phase. The methylene chloride solution was diluted with methylene chloride to a total solids content of 12 percent. 100 volumes of this organic solution containing the N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide was stirred with 100 volumes of hydrochloric acid having a normality of 0.06 N, the HCl being used in amount of 5.8 milliequivalents of acid based on 15.7 grams of solids. The aqueous acid and organic solutions were stirred together for about 15 minutes to a pH of the mixture of 2.7. The acid phase was separated from the organic solution by transferring the mixture to a separating vessel settling the layers, and decanting. The organic solution was then washed twice with 100 volumes of distilled water and separated from the water. The methylene chloride was then flashed off and the dried N-oxydiethylenecarbamyl-N'-oxydiethylenesulfenamide collected. The melting point of the N-oxydiethylenecarbamyl-N'-oxydiethylenesulfenamide was found to be 134.8° C. A sample of N-oxydiethylenecarbamyl-N'-oxydiethylenesulfenamide was aged in an air over at 100° C. for 60 minutes to test for stability. The melting point after aging was determined and found to be 133.0° C., for a ΔT of 1.8, this sample being very stable. When a control run was made without the acid wash, using only water washes, the unaged melting point was found to be 134.4° C. and the aged melting point was found to be 128.4° , for a ΔT of 6.0, which represents a very unstable product with unsatisfactory storage stability and product activity. was separated from the water phase The methylene chloride solution was diluted with methylene chloride to a total solids content of 12 percent 100 volumes of this organic solution containing the N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide The aqueous acid and organic solutions were stirred together for about 15 minutes to a pH of the mixture of 2.7 The acid phase was separated from the organic solution decanting The organic solution was then washed twice with 100 volumes of distilled water separated from the water the dried N-oxydiethylenecarbamyl-N'-oxydiethylenesulfenamide collected to be 134.8° C to be 133.0° C., for a ΔT of 1.8 wash to be 134.4° C. to be 128.4° , for a ΔT of 6.0, which

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide was prepared by reacting about 0.2 mole of morpholine and about 0.2 mole of N-chloromorpholine chloride with 0.2 mole of carbon disulfide in the presence of about 0.2 mole of NaOH and in a medium of water and chloroform. 34.8 grams (0.4 mole) of morpholine was added to 50 milliliters of chloroform and the solution cooled to 0° C. 110 grams of a solution of NaOCl at 13% by weight in water (0.2 mole) was added and the mixture stirred for 10 minutes at a temperature of about 10° C. 15.2 grams (0.2 mole) of carbon disulfide was then added and the mix stirred for 10 minutes at 10°±5° C. The mixture became thick and an additional 50 milliliters of chloroform was added. After 15 minutes of stirring, the mixture was allowed to settle and the non-aqueous phase was separated out. The chloroform was evaporated off under reduced pressure. The pale yellow crystals obtained were slurried in methanol, filtered out and dried. The yield of compound was 45.2 grams, 92% by weight of theoretical. The compound was identified by its IR spectrum, and it had a melting point of 128°-134° C. the mix stirred for 10 minutes at 10°±5° C After 15 minutes of stirring the non-aqueous phase was separated out The chloroform was evaporated off under reduced pressure The pale yellow crystals obtained filtered out dried