The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdon of Great Britain and Northern Ireland
대리인 / 주소
Kilpatrick Stockton LLP
인용정보
피인용 횟수 :
1인용 특허 :
3
초록▼
The invention describes the synthesis of novel mono-amine and di-amine derivatives of hexa-nitro-hexaazaisohexawurtzitane (CL-20). The synthesis is affected by the novel use of fluoroacylating compounds to protect the secondary amine groups of acylated precursors to CL-20 against nitrolysis. In so
The invention describes the synthesis of novel mono-amine and di-amine derivatives of hexa-nitro-hexaazaisohexawurtzitane (CL-20). The synthesis is affected by the novel use of fluoroacylating compounds to protect the secondary amine groups of acylated precursors to CL-20 against nitrolysis. In so doing the mono-amine and di-amine derivatives of CL-20 are rendered and which in turn may be subsequently utilized as intermediates to generate further novel derivatives with differing physical and chemical properties to the parent compound. Formula (I), wherein:--X═H, and Y═H or NO2.
대표청구항▼
The invention claimed is: 1. A method of producing a compound of formula (I) wherein X is H, and Y is H or NO2, comprising (1) fluoroacylation of a compound of formula (II) to protect non-acylated secondary amine groups at the n-4 positions, n-10 positions or both n-4 and n-10 positions and prod
The invention claimed is: 1. A method of producing a compound of formula (I) wherein X is H, and Y is H or NO2, comprising (1) fluoroacylation of a compound of formula (II) to protect non-acylated secondary amine groups at the n-4 positions, n-10 positions or both n-4 and n-10 positions and produce a fluoroacylated compound wherein formula (II) comprises: wherein X and Y are H, or X is Ac and Y is H, and Ac is--COCH3,--COCH2R, where R is C1-10 alkyl (linear or branched),--CH2--C6H5, or C1-10 arylalkyl; (2) nitrolysis of the fluoroacylated compound to produce a nitrolyzed compound, and (3) deprotection by solvolysis of the nitrolyzed compound. 2. The method of claim 1 wherein fluoroacylation is undertaken using a fluoroacylating reagent. 3. The method of claim 2 wherein the fluoroacylating reagent is a trifluoroacetylating reagent. 4. The method of claim 3 wherein the trifluoroacetylating reagent comprises trifluoroacetic anhydride, trifluoroethanoyl chloride, or a mixture of trifluoroacetic acid and trifluoroacetic anhydride. 5. The method of claim 1 wherein solvolysis comprises hydrolysis. 6. The method of claim 5 wherein solvolysis is undertaken using an alcohol or an alcohol in conjunction with a carboxylic acid salt. 7. The method of claim 1 wherein solvolysis is undertaken using sodium acetate in ethanol or sodium propionate in ethanol. 8. The method of claim 6 wherein the alcohol comprises methanol or ethanol. 9. The method of claim 1 wherein nitrolysis is undertaken using a nitrolysing reagent. 10. The method of claim 1 further comprising additional acylation prior to (1) wherein an acylating reagent is reacted with a compound of formula (II) with the proviso that X and Y are H. 11. The method of claim 10 wherein the acylating reagent is an acetylating reagent. 12. The method of claim 11 wherein the acetylating reagent comprises acetic anhydride and sodium acetate. 13. The method of claim 1 further comprising selectively deprotecting the nitrolyzed compound by solvolysis to produce a mono-amine derivative, followed by nitrolysis of the mono-amine derivative with the proviso that X and Y are H. 14. A method of making a compound of formula (III) wherein R1 and R2 are independently selected from: C1-C10 alkyl, C1-C10 alkylaryl,--CH2--C6H5, C1-C10 polyethers, C1-C10 fluorinated polyethers, C1-C10 fluorinated alkyl, CH2--C6F5, COR' where R'=C1-C10 alkyl,--COCl3,--COCCl3, CONHR", where R"=H, C1-C10 alkyl,--COCl3,--COCCl3, CONHCO2C2H5, C(O)CmF2mCpH2p+1, wherein m and p are integers and are independently chosen from the range 1 to 19 and wherein m+p is less than or equal to 20, and COCF3, comprising reacting the compound of formula (I) wherein X is H, and Y is H or NO2, with an acyl halide, an acyl anhydride or an isocyanato. 15. The method of claim 14 wherein the acyl halide comprises: C1-C10 alkylacyl halides, C1-C10 alkylaryl acyl halides, CH2-arylacyl halide, and R-acyl halides where R comprises C1-C10 polyethers, C1-C10 fluorinated polyethers, C1-C10 fluorinated alkyl, CH2-fluorinated phenyl, COR', where R'=C1-C10 alkyl, COCl3, COCCl3, CONHR", where R"=H, C1-C10 alkyl, COCl3, COCCl3, C(O)CmF2mCpH2p+1, wherein m and p are integers and are independently chosen from the range 1 to 19 and wherein m+p is less than or equal to 20, and COCF3. 16. The method of claim 14 wherein the acyl halide is an acyl chloride, an acyl bromide or an acetyl chloride. 17. The method of claim 14 wherein the acyl anhydride comprises C1-C10 alkylacylanhydride, C1-C10 alkylarylacylanhydride, CH2-arylacylanhydride, and R-acylanhydrides where R comprises C1-C10 polyethers, C1-C10 fluorinated polyethers, C1-C10 fluorinated alkyl, CH2-fluorinated phenyl, as well as R acyl anhydrides where R comprises: COR', where R'=C1-C10 alkyl, COCl3, COCCl3, CONHR", where R"=H, C1-C10 alkyl, COCl3, COCCl3, C(O)CmF2mCpH2p+1, wherein m and p are integers and are independently chosen from the range 1 to 19 and wherein m+p is less than or equal to 20, and COCF3. 18. The method of claim 14 wherein the acyl anhydride comprises acetic anhydride. 19. The method of claim 14 wherein the isocyanate comprises N-(chlororcarbonyl)isocyanate or trichloroacetyl isocyanate. 20. The method of claim 14 wherein the compound of formula (I) is reacted with an isocyanate to form a product that is reacted with an alcohol. 21. The method of claim 20 wherein the alcohol is methanol.
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이 특허에 인용된 특허 (3)
Wardle Robert B. ; Hinshaw Jerald C., Method for making new polycyclic polyamides as precursors for energetic polycyclic polynitramine oxidizers.
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