Process for preparing 1,5-diazido-3-nitrazapentane

Claim 2

A solvent process for making 1,5-diazido-3-nitrazapentane comprising the sequential steps of nitrating diethanolamine with nitric acid in a first halogenated solvent to make the intermediate 1,5-dinitrato-3-nitrazapentane, solvent transferring said intermediate from the first halogenated solvent to a second solvent selected from the group consisting of dimethylsulfoxide and dimethylformamide, reacting said intermediate with sodium azide to form 1,5-diazido-3-nitrazapentane as product in said second solvent, and solvent transferring said product from said second solvent to a third halogenated solvent.

Claim 3

The process of claim 1, including the steps of purifying said intermediate in solution in the first halogenated solvent and purifying said product in solution in said third halogenated solvent.

Claim 4

The process of claim 1, including the further step of solvent transferring said product from said third halogenated solvent to ethyl acetate.

Claim 5

The process of claim 1, said step of solvent transferring said intermediate comprising adding said second solvent to said first halogenated solvent solution of said intermediate, and subjecting the resulting solution to a vacuum to remove said halogenated solvent.

Claim 6

The process of claim 1, said step of solvent transferring said product comprising adding said third halogenated solvent to said second solvent solution of said product and washing the resulting solution with water to remove said second solvent, and leaving said product in solution in said third halogenated solvent.

Claim 7

The process of claim 1, said first and third halogenated solvents comprising methylene chloride.

Claim 8

The process of claim 1, said second solvent being dimethylsulfoxide.

Claim 9

The process of claim 6, said second solvent being dimethylsulfoxide, and including the steps of purifying said intermediate and said product in solution in said methylene chloride.

Claim 10

The process of claim 8, including the further step of solvent transferring said product from said methylene chloride to ethyl acetate by adding ethyl acetate to said methylene chloride solution of said product, and distilling off said methylene chloride, and leaving said product in solution in said ethyl acetate.

Claim 11

A process for making 1,5-diazido-3-nitrazapentane from 1,5-dinitrato-3-nitrazapentane, both of said compounds being prepared in solution, comprising the steps of nitrating diethanolomine with nitric acid in a first halogenated solvent selected from the group consisting of methylene chloride, carbon tetrachloride, chloroform and ethylene dichloride, employing an excess of nitric acid, and in the presence of acetic anhydride and hydrochloric acid, to make the intermediate 1,5-dinitrato-3-nitrazapentane, solvent transferring said intermediate from the first halogenated solvent to dimethylsulfoxide, by adding dimethylsulfoxide to the first halogenated solvent solution of said intermediate and subjecting the resulting solution to a vacuum to remove said first halogenated solvent, and leaving a solution of said intermediate in dimethylsulfoxide, adding sodium azide to said halogenated solvent solution of said intermediate, in an amount such as to produce a 5-20% excess of NaN 3 over said intermediate, and heating the resulting solution to a temperature of about 50° to about 90° C. to form 1,5-diazido-3-nitrazapentane as product, and solvent transferring said product from the dimethylsulfoxide to a second halogenated solvent selected from the group consisting of methylene chloride, carbon tetrachloride, chloroform and ethylene dichloride, by adding said second halogenated solvent to said dimethylsulfoxide solution of said product, and washing the resulting solution with water to remove dimethylsulfoxide, and leaving said product in solution in said second organic solvent.

Claim 12

A process for making 1,5-diazido-3-nitrazapentane from 1,5-dinitrato-3-nitrazapentane, both of said compounds being prepared in solution, comprising the steps of nitrating diethanolomine with nitric acid in a first halogenated solvent selected from the group consisting of methylene chloride, carbon tetrachloride, chloroform and ethylene dichloride, employing an excess of nitric acid, and in the presence of acetic anhydride and hydrochloric acid, to make the intermediate 1,5-dinitrato-3-nitrazapentane, solvent transferring said intermediate from the first halogenated solvent to dimethylsulfoxide, by adding dimethylsulfoxide to the first halogenated solvent solution of said intermediate and subjecting the resulting solution to a vacuum to remove said first halogenated solvent, and leaving a solution of said intermediate in dimethylsulfoxide, adding sodium azide to said halogenated solvent solution of said intermediate, in an amount such as to produce a 5-20% excess of NaN 3 over said intermediate, and heating the resulting solution to a temperature of about 50° to about 90° C. to form 1,5-diazido-3-nitrazapentane as product, and solvent transferring said product from the dimethylsulfoxide to a second halogenated solvent selected from the group consisting of methylene chloride, carbon tetrachloride, chloroform and ethylene dichloride, by adding said second halogenated solvent to said dimethylsulfoxide solution of said product, and washing the resulting solution with water to remove dimethylsulfoxide, and leaving said product in solution in said second organic solvent.

Claim 13

The process of claim 10, including the steps of purifying said intermediate in solution in the first halogenated solvent and purifying said product in solution in said second halogenated solvent.

Claim 14

The process of claim 11, said first halogenated solvent comprising methylene chloride.

Claim 15

The process of claim 12, said second halogenated solvent comprising methylene chloride, and including the further step of solvent transferring said product from said methylene chloride to ethyl acetate, by adding ethyl acetate to said methylene chloride solution of said product and distilling off said methylene chloride, leaving an ethyl acetate solution of said product.

Claim 16

In a process for making 1,5-diazido-3-nitrazapentane from the intermediate 1,5-dinitrato-3-nitrazapentane, by nitrating diethanolamine with nitric acid in a halogenated solvent to make said intermediate and reacting said intermediate with sodium azide at elevated temperature to form 1,5-diazido-3-nitrazapentane, the improvement which comprises the steps of solvent transferring said intermediate from said halogenated solvent to a solvent having a boiling point higher than the elevated temperature of reaction of the 1,5-dinitrato-3-nitrazapentane and sodium azide, and which dissolves both reactants and is soluble in water, and following said reaction of 1,5-dinitrato-3-nitrazapentane with sodium azide to form 1,5-diazido-3-nitrazapentane as product, solvent transferring said product from said higher boiling solvent to a halogenated solvent.

Claim 17

In a process for making 1,5-diazido-3-nitrazapentane from the intermediate 1,5-dinitrato-3-nitrazapentane, by nitrating diethanolamine with nitric acid in a halogenated solvent to make said intermediate and reacting said intermediate with sodium azide at elevated temperature to form 1,5-diazido-3-nitrazapentane, the improvement which comprises the steps of solvent transferring said intermediate from said halogenated solvent to a solvent having a boiling point higher than the elevated temperature of reaction of the 1,5-dinitrato-3-nitrazapentane and sodium azide, and which dissolves both reactants and is soluble in water, and following said reaction of 1,5-dinitrato-3-nitrazapentane with sodium azide to form 1,5-diazido-3-nitrazapentane as product, solvent transferring said product from said higher boiling solvent to a halogenated solvent.

Claim 18

The process of claim 14, said higher boiling solvent having a boiling point greater than 90° C.

Claim 19

The process of claim 15, said higher boiling solvent selected from the group consisting of dimethylsulfoxide and dimethylformamide.