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    • 4. 发明申请
    • Preparation for the production of 1,2,4-triazolymethyl-oxiranes
    • 制备1,2,4-三唑甲基环氧乙烷
    • US20050176967A1
    • 2005-08-11
    • US10516727
    • 2003-06-06
    • Rainer NoackMichael SanderMichael Henningsen
    • Rainer NoackMichael SanderMichael Henningsen
    • C07D405/06C07D521/00C07D45/02
    • C07D249/08C07D231/12C07D233/56
    • The present invention relates to a process for the preparation of 1,2,4-triazol-1-ylmethyloxiranes of the formula I in which A and B are identical or different and, independently of one another, are C1-C4-alkyl, phenyl-C1-C2-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, tetrahydropyranyl, tetrahydrofuranyl, dioxanyl or phenyl, where the phenyl radical can carry one to three substituents chosen from the group: halogen, nitro, C1-C4-alkyl, Cl-C4-alkyloxy, phenoxy, amino, C1-C2-haloalkyl or phenylsulfonyl, which comprises reacting a) an oxirane of the formula II in which A and B have the meanings given above and L is a nucleophilically substitutable leaving group, with 4-amino-1,2,4-triazole of the formula III to give 4-amino-1,2,4-triazolium salts of the formula IV and b) deaminating the 4-amino-1,2,4-triazolium salts IV with alkali metal nitrites and acid or organic nitrites to give 1,2,4-triazol-1-ylmethyloxiranes of the formula I, and to 4-aminotriazolium salts of the formula IV as intermediates.
    • 本发明涉及制备式I的1,2,4-三唑-1-基甲基环氧烷的方法,其中A和B相同或不同,且彼此独立地为C 1〜 C 1 -C 4 - 亚烷基,苯基-C 1 -C 2 - 烷基,C 3 -C C 6 -C 6 - 环烷基,C 3 -C 6 - 环烯基,四氢吡喃基,四氢呋喃基,二烷基或苯基,其中苯基可以携带一至三个 选自以下的取代基:卤素,硝基,C 1 -C 4 - 烷基,C 1 -C 4 - 烷氧基,苯氧基,氨基,C 1 -C 2 - 卤代烷基或苯基磺酰基,其包括使a)式A的环氧乙烷与A和B具有式 L是具有式III的4-氨基-1,2,4-三唑的亲核可取代的离去基团,得到式IV的4-氨基-1,2,4-三唑鎓盐,和b)脱氨基 具有碱金属元素的4-氨基-1,2,4-三唑鎓盐IV l亚硝酸盐和酸或有机亚硝酸盐,得到式I的1,2,4-三唑-1-基甲基环氧乙烷和作为中间体的式IV的4-氨基三唑鎓盐。
    • 10. 发明授权
    • Preparation for the production of 1,2,4-triazolylmethyl-oxiranes
    • 制备1,2,4-三唑基甲基环氧乙烷
    • US07368464B2
    • 2008-05-06
    • US10516727
    • 2003-06-06
    • Rainer NoackMichael SanderMichael Henningsen
    • Rainer NoackMichael SanderMichael Henningsen
    • A61K31/41C07D249/08
    • C07D249/08C07D231/12C07D233/56
    • The present invention relates to a process for the preparation of 1,2,4-triazol-1-ylmethyloxiranes of the formula I in which A and B are identical or different and, independently of one another, are C1-C4-alkyl, phenyl-C1-C2-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, tetrahydropyranyl, tetrahydrofuranyl, dioxanyl or phenyl, where the phenyl radical can carry one to three substituents chosen from the group: halogen, nitro, C1-C4-alkyl, Cl-C4-alkyloxy, phenoxy, amino, C1-C2-haloalkyl or phenylsulfonyl, which comprises reacting a) an oxirane of the formula II in which A and B have the meanings given above and L is a nucleophilically substitutable leaving group, with 4-amino-1,2,4-triazole of the formula III to give 4-amino-1,2,4-triazolium salts of the formula IV and b) deaminating the 4-amino-1,2,4-triazolium salts IV with alkali metal nitrites and acid or organic nitrites to give 1,2,4-triazol-1-ylmethyloxiranes of the formula I, and to 4-aminotriazolium salts of the formula IV as intermediates.
    • 本发明涉及制备式I的1,2,4-三唑-1-基甲基环氧烷的方法,其中A和B相同或不同,且彼此独立地为C 1〜 C 1 -C 4 - 亚烷基,苯基-C 1 -C 2 - 烷基,C 3 -C C 6 -C 6 - 环烷基,C 3 -C 6 - 环烯基,四氢吡喃基,四氢呋喃基,二烷基或苯基,其中苯基可以携带一至三个 选自以下的取代基:卤素,硝基,C 1 -C 4 - 烷基,C 1 -C 4 - 烷氧基,苯氧基,氨基,C 1 -C 2 - 卤代烷基或苯基磺酰基,其包括使a)式A的环氧乙烷与A和B具有式 L是具有式III的4-氨基-1,2,4-三唑的亲核可取代的离去基团,得到式IV的4-氨基-1,2,4-三唑鎓盐,和b)脱氨基 具有碱金属元素的4-氨基-1,2,4-三唑鎓盐IV l亚硝酸盐和酸或有机亚硝酸盐,得到式I的1,2,4-三唑-1-基甲基环氧乙烷和作为中间体的式IV的4-氨基三唑鎓盐。