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US 4,066,833 AGranted
2,3,7,8-Tetraazaspiro [4.4]nonane, 2,3,7,8-tetraazaspiro-[4.4]nona-2,7-diene and derivatives
AssigneeThe United States of America as represented by the Secretary of the Navy
InventorArnold T. Nielsen
Life of this patent
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Abstract
Synthetic routes to 2,3,7,8-tetraazaspiro [4.4] nonane, its bispicrate sa 2,3,7,8-tetraazaspiro [4.4]nona-2,7-diene, and 3,8-dicarbomethoxy-2,3,7,8-tetraazaspiro [4.4]nona-1,6-diene. The compounds are useful as high density fuels.
Claims5
2,3,7,8-Tetraazaspiro[4.4]nonane.
2,3,7,8-Tetraazasiro[4.4]nona-2,7-diene.
The bispicrate salt of 2,3,7,8-tetraazaspiro [4,4]4.4 nonane.
3,8-Dicarbomethoxy-2,3,7,8-tetraazaspiro [4.4]nona-1,6-diene.
A method for preparing 2,3,7,8-tetraazaspiro [4.4]nonane comprising the steps of:
- A. preparing a solution of 4-phenylurazole in ethanolic potassium ethoxide and a solution of pentaerythrityl tetrabromide in dimethylformamide, forming a reaction mixture from the two solutions reacting it to cause 2,2'-diphenyl-1,1'3,3'-tetraoxo-6,6'-spirobi[hexahydropyrazobi 1,2-a]-s-triazole to be formed and recovering the s-triazole;
- B. reacting the s-triazole from steps A. with sodium hydroxide and hydrochloric acid in succession to form 2,3,7,8-tetraazaspiro[4.4]nonane bishydrochloride and recovering the bishydrochloride;
- C. reacting the bishydrochloride from step B. with potassium bisulfate to form 2,3,7,8-tetraazaspiro [4.4]nonane sulfate and recovering the sulfate;
- and
- D. subjecting the sulfate to ammonia to form said 2,3,7,8-tetraazaspiro[4.4]nonane.
2 more elements
Dependencies are inferred from the claim text.