Method for making 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-dinitro-1,5-diazocine (HNFX)
US7632943B1 · kind B1 · utility
Assignee
Inventors
Key dates
| Filing date | Dec 10, 2004 |
| Grant date | Dec 15, 2009 |
| Priority date | — |
| Expiry date | Jul 24, 2025 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A novel reaction scheme is presented for making a 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-diazocinium salt, such as HNFX, from a tetrahydro-1,5-diazocine-3,7(2H,6H)-dione that does not employ N-nitrolysis,—but that instead requires protolytic N-deprotection, or protolytic denosylation, (i.e., the nosyl N-protecting group is replaced with protons, forming the corresponding protonated amine or ammonium derivative). In summary, the present method subjects a suitably N-protected dione to difluoramination followed by protolytic N-deprotection by addition of a superacid and subsequent nitration utilizing an electrophilic nitrating agent to yield the diazocinium salt.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.