New difluoramino compounds

摘要

A difluoramino compound is prepared by reacting difluoramine in an inert atmosphere in the presence of an acid catalyst with a compound of the general formula wherein R1 is a group having next to the nitrogen atom an electron attracting group, for example, carbonyl, >C=NH, N-substituted >C=N, triazine ring, or sulphonyl, and R2, R3 and R4 are hydrogen, alkyl, or substituted alkyl; two of the groups R1, R2, R3 and R4 may be joined in a ring; R4 may be the group In the reaction the -OR3 groups are replaced by -NF2 groups. The reaction may be carried out by refluxing with excess difluoramine at -23 DEG C. under nitrogen using 96% sulphuric acid as catalyst. In Examples (1) and (2) N,N1-dimethylol urea or N,N1-di-(methoxymethyl) urea is converted to N,N1-bis-(difluoraminomethyl) urea; (3) N,N1-di-(methoxymethyl) uron is reacted to form tetrakis-(difluoraminomethyl) urea and N,N,N1-tris-(difluoraminomethyl) urea; (4) hexakis-(methoxymethyl) melamine is converted to hexakis-(difluoraminomethyl) melamine; (5)-(7) 4,5-dihydroxy-, 4,5-dimethoxy, or 4,5-diethoxyimidazolidin-2-one is reacted to form 4,5-bis-(difluoramino) imidazolidin-2-one; (8) 1,3-di-(methoxymethyl) - 4,5 - dimethoxy - imidazolidin-2-one is converted to 1,3-bis-(difluoraminomethyl) - 4,5 - bis - (difluoramino)-imidazolidin - 2 - one; (9) 1,3 - diformyl-4,5 - dihydroxy - imidazolidine is reacted to form 1,3 - diformyl - 4,5 - bis - (difluoramino) imidazolidine; (10) 1,2 - diformamido - 1,2-dihydroxy ethane is converted to 1,2-diformamido - 1,2 - bis - (difluoramino) ethane; (11) and (12) 1,2-diacetamido-1,2-dihydroxy ethane or 1,2 - diacetamido - 1,2 - dimethoxy ethane is reacted to form 1,2-diacetamido-1,2-bis-(difluoramino) ethane; (13) and (14) 1,2-di-(carbethoxyamino)-1,2-dihydroxy ethane or 1,2-di - (carbethoxyamino) - 1,2 - dimethoxy ethane is converted to 1,2-di-(carbethoxyamino)-1,2-bis-(difluoramino) ethane; (15) hexamethylolmelamine monohydrate is converted to hexakis-(difluoraminomethyl) melamine; (16) 1,2,2-tri-(carbethoxyamino) ethanol is reacted to form 1,2,2 - tri - (carbethoxyamino) - 1 - (difluoramino) ethane. Several of the products are claimed per se. The compounds are useful as high energy constituents of explosives.