DD201885A5 - Verfahren zur herstellung von n-(halomethyl)-acylamiden - Google Patents
Verfahren zur herstellung von n-(halomethyl)-acylamiden Download PDFInfo
- Publication number
- DD201885A5 DD201885A5 DD81235203A DD23520381A DD201885A5 DD 201885 A5 DD201885 A5 DD 201885A5 DD 81235203 A DD81235203 A DD 81235203A DD 23520381 A DD23520381 A DD 23520381A DD 201885 A5 DD201885 A5 DD 201885A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- radical
- item
- formula
- chloromethyl
- compound
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 56
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 7
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 7
- -1 haloalkyl radical Chemical class 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 18
- 150000003254 radicals Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 abstract description 14
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000003921 oil Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002243 precursor Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- 150000003869 acetamides Chemical class 0.000 description 2
- 150000003931 anilides Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- SQGUQSRDWXDLIH-UHFFFAOYSA-N 2,3-dichloropropanamide Chemical compound NC(=O)C(Cl)CCl SQGUQSRDWXDLIH-UHFFFAOYSA-N 0.000 description 1
- MGSXWVBFRJCQMZ-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylcyclohexen-1-yl)-n-(methoxymethyl)acetamide Chemical compound COCN(C(=O)CCl)C1=C(C)CCCC1C MGSXWVBFRJCQMZ-UHFFFAOYSA-N 0.000 description 1
- GPPSFMVBXJGOQO-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylcyclohexen-1-yl)acetamide Chemical compound CC1CCCC(C)=C1NC(=O)CCl GPPSFMVBXJGOQO-UHFFFAOYSA-N 0.000 description 1
- FPQQSNUTBWFFLB-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CCl FPQQSNUTBWFFLB-UHFFFAOYSA-N 0.000 description 1
- LPMANECYGPQBOX-UHFFFAOYSA-N 2-chloro-n-(2-methylphenyl)acetamide Chemical compound CC1=CC=CC=C1NC(=O)CCl LPMANECYGPQBOX-UHFFFAOYSA-N 0.000 description 1
- STVRVHDMZHCKDW-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,5-dimethylcyclopenten-1-yl)acetamide Chemical compound CC1CCC(C)=C1N(CCl)C(=O)CCl STVRVHDMZHCKDW-UHFFFAOYSA-N 0.000 description 1
- PDQMMZXYWKOZHY-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(CCl)C(=O)CCl PDQMMZXYWKOZHY-UHFFFAOYSA-N 0.000 description 1
- QHVMCJZPSNGMJX-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,6-dimethoxyphenyl)acetamide Chemical compound COC1=CC=CC(OC)=C1N(CCl)C(=O)CCl QHVMCJZPSNGMJX-UHFFFAOYSA-N 0.000 description 1
- DGGUZRQZLZDYGG-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1N(CCl)C(=O)CCl DGGUZRQZLZDYGG-UHFFFAOYSA-N 0.000 description 1
- UTPRVZATQNGTNH-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-[2-methyl-6-(2-methylpropoxy)phenyl]acetamide Chemical compound CC(C)COC1=CC=CC(C)=C1N(CCl)C(=O)CCl UTPRVZATQNGTNH-UHFFFAOYSA-N 0.000 description 1
- CIRVBUOHMNOQEJ-UHFFFAOYSA-N 2-chloro-n-(methoxymethyl)acetamide Chemical compound COCNC(=O)CCl CIRVBUOHMNOQEJ-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- GIEZWIDCIFCQPS-UHFFFAOYSA-N 3-ethyl-3-methylpentane Chemical compound CCC(C)(CC)CC GIEZWIDCIFCQPS-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 102100037978 InaD-like protein Human genes 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- 101100070104 Mus musculus Hacl1 gene Proteins 0.000 description 1
- JOCBASBOOFNAJA-UHFFFAOYSA-N N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid Chemical compound OCC(CO)(CO)NCCS(O)(=O)=O JOCBASBOOFNAJA-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 101150003018 Patj gene Proteins 0.000 description 1
- 108010013381 Porins Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- AMANDCZTVNQSNB-UHFFFAOYSA-N glyoxamide Chemical class NC(=O)C=O AMANDCZTVNQSNB-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- HRTKPJQRVDDTOR-UHFFFAOYSA-N n-(bromomethyl)-2-chloro-n-(2,6-dimethylcyclohexen-1-yl)acetamide Chemical compound CC1CCCC(C)=C1N(CBr)C(=O)CCl HRTKPJQRVDDTOR-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 102000007739 porin activity proteins Human genes 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/211,608 US4311858A (en) | 1980-12-01 | 1980-12-01 | Process for producing N-(halomethyl) acyl-amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD201885A5 true DD201885A5 (de) | 1983-08-17 |
Family
ID=22787633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81235203A DD201885A5 (de) | 1980-12-01 | 1981-11-27 | Verfahren zur herstellung von n-(halomethyl)-acylamiden |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4311858A (cs) |
| EP (1) | EP0053495B1 (cs) |
| JP (1) | JPS57120557A (cs) |
| KR (1) | KR850001601B1 (cs) |
| AR (1) | AR229168A1 (cs) |
| AT (1) | ATE8877T1 (cs) |
| AU (1) | AU542134B2 (cs) |
| BR (1) | BR8107773A (cs) |
| CA (1) | CA1178614A (cs) |
| CS (1) | CS231186B2 (cs) |
| DD (1) | DD201885A5 (cs) |
| DE (1) | DE3165449D1 (cs) |
| ES (1) | ES8207131A1 (cs) |
| GB (1) | GB2088865B (cs) |
| HU (1) | HU188159B (cs) |
| IL (1) | IL64402A (cs) |
| MX (1) | MX6900E (cs) |
| NO (1) | NO153100C (cs) |
| NZ (1) | NZ199109A (cs) |
| PL (1) | PL130528B1 (cs) |
| RO (1) | RO83714B (cs) |
| YU (1) | YU277881A (cs) |
| ZA (1) | ZA818300B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731451A (en) * | 1980-03-25 | 1988-03-15 | Monsanto Company | N-((2-oxo-3(2H)benzothiazolyl)methyl)-2-chloroacetanilides |
| DE3123731A1 (de) * | 1981-06-15 | 1982-12-30 | Basf Ag, 6700 Ludwigshafen | Chloressigsaeurecyclohexylamide, ihre herstellung, ihre verwendung zur herbizidbekaempfung und mittel dafuer |
| AT382870B (de) * | 1982-02-09 | 1987-04-27 | Sandoz Ag | Verfahren zur herstellung neuer chloracetamide |
| DE3206660A1 (de) * | 1982-02-25 | 1983-09-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von o-acylamidomethylbenzyl-halogeniden |
| JP3449435B2 (ja) * | 1993-12-24 | 2003-09-22 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料の処理方法 |
| CN111302968B (zh) * | 2020-03-20 | 2021-06-08 | 中国科学院上海有机化学研究所 | 一种酰胺氮三氟甲基化合物的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259540A (en) * | 1961-02-13 | 1966-07-05 | Murphy Chemical Ltd | Stabilized insecticidal composition containing an o, o-dimethyl s-(n-alkoxymethyl) carbamoylmethyl phosphorothiolothionate |
| US3574746A (en) * | 1967-06-05 | 1971-04-13 | Monsanto Co | N-(cycloalken-1-yl) alpha-haloacetamides |
| US3637847A (en) * | 1969-09-03 | 1972-01-25 | Monsanto Co | N-haloalkyl-anilides |
| DE2351297A1 (de) * | 1973-10-12 | 1975-04-24 | Bayer Ag | N,n-bishalogenmethyl-acrylamide |
| ES465723A1 (es) * | 1976-12-29 | 1978-10-01 | Monsanto Co | Procedimiento para la preparacion y recuperacion de haloge- noacilamidas. |
| DE2854599A1 (de) * | 1978-12-18 | 1980-06-26 | Basf Ag | Substituierte n-halogenmethylanilide und verfahren zu ihrer herstellung und verwendung |
-
1980
- 1980-12-01 US US06/211,608 patent/US4311858A/en not_active Expired - Lifetime
-
1981
- 1981-11-26 YU YU02778/81A patent/YU277881A/xx unknown
- 1981-11-27 ES ES507500A patent/ES8207131A1/es not_active Expired
- 1981-11-27 DD DD81235203A patent/DD201885A5/de unknown
- 1981-11-27 EP EP81305618A patent/EP0053495B1/en not_active Expired
- 1981-11-27 DE DE8181305618T patent/DE3165449D1/de not_active Expired
- 1981-11-27 AT AT81305618T patent/ATE8877T1/de not_active IP Right Cessation
- 1981-11-30 MX MX819795U patent/MX6900E/es unknown
- 1981-11-30 AU AU78110/81A patent/AU542134B2/en not_active Ceased
- 1981-11-30 IL IL64402A patent/IL64402A/xx unknown
- 1981-11-30 CS CS818833A patent/CS231186B2/cs unknown
- 1981-11-30 GB GB8136035A patent/GB2088865B/en not_active Expired
- 1981-11-30 JP JP56190946A patent/JPS57120557A/ja active Pending
- 1981-11-30 NO NO814074A patent/NO153100C/no unknown
- 1981-11-30 PL PL1981234036A patent/PL130528B1/pl unknown
- 1981-11-30 ZA ZA818300A patent/ZA818300B/xx unknown
- 1981-11-30 KR KR1019810004641A patent/KR850001601B1/ko not_active Expired
- 1981-11-30 HU HU813593A patent/HU188159B/hu unknown
- 1981-11-30 AR AR287624A patent/AR229168A1/es active
- 1981-11-30 BR BR8107773A patent/BR8107773A/pt unknown
- 1981-11-30 CA CA000391187A patent/CA1178614A/en not_active Expired
- 1981-11-30 RO RO105905A patent/RO83714B/ro unknown
- 1981-11-30 NZ NZ199109A patent/NZ199109A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS883381A2 (en) | 1984-02-13 |
| IL64402A0 (en) | 1982-02-28 |
| AR229168A1 (es) | 1983-06-30 |
| RO83714B (ro) | 1984-05-30 |
| HU188159B (en) | 1986-03-28 |
| AU542134B2 (en) | 1985-02-07 |
| GB2088865B (en) | 1985-06-12 |
| ES507500A0 (es) | 1982-09-01 |
| US4311858A (en) | 1982-01-19 |
| DE3165449D1 (en) | 1984-09-13 |
| CS231186B2 (en) | 1984-10-15 |
| MX6900E (es) | 1986-10-10 |
| ZA818300B (en) | 1983-01-26 |
| NO153100B (no) | 1985-10-07 |
| PL130528B1 (en) | 1984-08-31 |
| JPS57120557A (en) | 1982-07-27 |
| GB2088865A (en) | 1982-06-16 |
| EP0053495B1 (en) | 1984-08-08 |
| NZ199109A (en) | 1985-12-13 |
| AU7811081A (en) | 1982-06-10 |
| BR8107773A (pt) | 1982-08-31 |
| KR830007513A (ko) | 1983-10-21 |
| CA1178614A (en) | 1984-11-27 |
| ATE8877T1 (de) | 1984-08-15 |
| YU277881A (en) | 1983-09-30 |
| PL234036A1 (cs) | 1982-07-05 |
| EP0053495A1 (en) | 1982-06-09 |
| NO814074L (no) | 1982-06-02 |
| RO83714A (ro) | 1984-04-12 |
| ES8207131A1 (es) | 1982-09-01 |
| NO153100C (no) | 1986-01-15 |
| KR850001601B1 (ko) | 1985-10-24 |
| IL64402A (en) | 1984-11-30 |
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