METHOD FOR PRODUCING [1,2,3,4]-TETRAZINO-[5,6-e]-[1,2,3,4]-TETRAZINO-1,3,6,8-TETRAOXIDE Russian patent published in 2016 - IPC C07D487/04 

FIELD: chemistry.

SUBSTANCE: invention relates to method for producing [1,2,3,4]-tetrazino-[5,6-e]-[1,2,3,4]-tetrazino-1,3,6,8-tetraoxide of formula:

,

process consists in that 4-amino-2-(tert-butyl)-5-(tert-butyl-NNO-azoxy)-1,2,3-triazol-1-N-oxide is subjected to nitrous acid salt treatment in mixture of acetic acid and diethyl ether, resulted therein 2-(tert-butyl)-5-(tert-butyl-NNO-azoxy)-1,2,3-triazol-1-N-oxide is treated with lithium salt of N,N-dialkylamine in mixture of hexane and polar organic solvent at low temperature with subsequent acidification of formed precipitate, and obtained 2,2-bis-(tert-butyl-NNO-azoxy)-acetonitrile reacts with alkyl mercaptan and trialkylamine in non-polar organic solvent medium, with subsequent treatment of formed 2-(tert-butyl)-1-[1-(tert-butyl-NNO-azoxy)-2-imino-2-(alkylsulfanyl)-ethyl]-diazen-1-oxide with nitric acid in presence of sulfuric acid in acetic anhydride medium, obtained therein 2-(tert-butyl)-1-[1-(tert-butyl-NNO-azoxy)-2-(nitroimino)-2-(alkylsulfanyl)-ethyl]-diazen-1-oxide reacts with alkali metal alcoholate in alcohol, with subsequent evaporation of reaction mixture and processing obtained residue with silver nitrate in acetonitrile, obtained therein silver salt of 2-(tert-butyl)-1-[1-(tert-butyl-NNO-azoxy)-2-(nitroimino)-2-(alkylsulfanyl)-ethyl]-diazen-1-oxide is treated with isopropyl bromide in low-polar aprotic solvent medium, resulted therein 2-[2.2-bis-(tert-butyl-NNO-azoxy)-1-(alkylsulfanyl)-vinyl]-1-(isopropoxy)-diazen-1-oxide reacts with peracid in non-polar organic solvent medium, to form 2-[2.2-bis-(tert-butyl-NNO-azoxy)-1-(alkylsulfinyl)-vinyl]-1-(isopropoxy)-diazen-1-oxide, subsequent treatment thereof with peracid in non-polar organic solvent medium leads to formation of 2-[2.2-bis-(tert-butyl-NNO-azoxy)-1-(alkylsulfonyl)-vinyl]-1-(isopropoxy)-diazen-1-oxide, which reacts with excess of boron trifluoride etherate in presence of non-polar organic solvent with subsequent evaporation of reaction mixture and processing obtained residue with ammonia in polar organic solvent medium, and resulted 5-amino-6-(tert-butyl-NNO-azoxy)-1,2,3,4-tetrazin-1,3-dioxide is successively reacted with nitric acid and sulfuric acid in acetic anhydride medium with further separation of end product I.

EFFECT: technical effect: method for producing compound of formula (I) is developed, which can be used as component of high-pulse, solid rocket propellants and powerful explosive compounds.

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