JPS5833868B2 - ベ−タ − ハロゲンアルキルアミノスルホニルハロゲニドノ セイホウ - Google Patents
ベ−タ − ハロゲンアルキルアミノスルホニルハロゲニドノ セイホウInfo
- Publication number
- JPS5833868B2 JPS5833868B2 JP50021073A JP2107375A JPS5833868B2 JP S5833868 B2 JPS5833868 B2 JP S5833868B2 JP 50021073 A JP50021073 A JP 50021073A JP 2107375 A JP2107375 A JP 2107375A JP S5833868 B2 JPS5833868 B2 JP S5833868B2
- Authority
- JP
- Japan
- Prior art keywords
- aziridine
- chloride
- carbon atoms
- reaction
- sulfuryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229910052736 halogen Inorganic materials 0.000 title description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- -1 sulfuryl halide Chemical class 0.000 claims description 14
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 239000007858 starting material Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000013076 target substance Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000005935 Sulfuryl fluoride Substances 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- NHPIGLPRLKEFTQ-UHFFFAOYSA-N n-methylethenimine Chemical compound CN=C=C NHPIGLPRLKEFTQ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
- JCMGUODNZMETBM-UHFFFAOYSA-N arsenic trifluoride Chemical compound F[As](F)F JCMGUODNZMETBM-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IXPAAHZTOUOJJM-UHFFFAOYSA-N sulfuryl chloride fluoride Chemical compound FS(Cl)(=O)=O IXPAAHZTOUOJJM-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
- MKCZABZZOZOQTK-UHFFFAOYSA-N 1,2-dimethyl-3-phenylaziridine Chemical compound CN1C(C)C1C1=CC=CC=C1 MKCZABZZOZOQTK-UHFFFAOYSA-N 0.000 description 1
- YZXPJVLVVIQNPF-UHFFFAOYSA-N 1-(2-chloroethyl)aziridine Chemical compound ClCCN1CC1 YZXPJVLVVIQNPF-UHFFFAOYSA-N 0.000 description 1
- ZESWABYAKZEPQB-UHFFFAOYSA-N 1-(2-ethoxyethyl)aziridine Chemical compound CCOCCN1CC1 ZESWABYAKZEPQB-UHFFFAOYSA-N 0.000 description 1
- QESKGSBCEIGZHD-UHFFFAOYSA-N 1-(2-methoxyethyl)aziridine Chemical compound COCCN1CC1 QESKGSBCEIGZHD-UHFFFAOYSA-N 0.000 description 1
- FJLAEPRFEAIKHC-UHFFFAOYSA-N 1-(2-methylbutyl)aziridine Chemical compound CCC(C)CN1CC1 FJLAEPRFEAIKHC-UHFFFAOYSA-N 0.000 description 1
- BCLOICLXYSBVNH-UHFFFAOYSA-N 1-(3-fluoropropyl)aziridine Chemical compound FCCCN1CC1 BCLOICLXYSBVNH-UHFFFAOYSA-N 0.000 description 1
- HWPQFYNSYAJJOT-UHFFFAOYSA-N 1-(3-hexoxypropyl)aziridine Chemical compound CCCCCCOCCCN1CC1 HWPQFYNSYAJJOT-UHFFFAOYSA-N 0.000 description 1
- ORLFBUHNIIXTFT-UHFFFAOYSA-N 1-(3-methoxypropyl)aziridine Chemical compound COCCCN1CC1 ORLFBUHNIIXTFT-UHFFFAOYSA-N 0.000 description 1
- ALRLOOGIRZGIJI-UHFFFAOYSA-N 1-(4-methoxybutyl)aziridine Chemical compound COCCCCN1CC1 ALRLOOGIRZGIJI-UHFFFAOYSA-N 0.000 description 1
- HORYQQFPUDMCAO-UHFFFAOYSA-N 1-(5-methoxypentyl)aziridine Chemical compound COCCCCCN1CC1 HORYQQFPUDMCAO-UHFFFAOYSA-N 0.000 description 1
- OKFXPPXKRABEBT-UHFFFAOYSA-N 1-(6-butoxyhexyl)aziridine Chemical compound CCCCOCCCCCCN1CC1 OKFXPPXKRABEBT-UHFFFAOYSA-N 0.000 description 1
- VOTTWAIHZXGNCG-UHFFFAOYSA-N 1-(methoxymethyl)aziridine Chemical compound COCN1CC1 VOTTWAIHZXGNCG-UHFFFAOYSA-N 0.000 description 1
- PJNRMWOACZFGCJ-UHFFFAOYSA-N 1-butan-2-ylaziridine Chemical compound CCC(C)N1CC1 PJNRMWOACZFGCJ-UHFFFAOYSA-N 0.000 description 1
- XIEJPTDTTYFCJM-UHFFFAOYSA-N 1-butylaziridine Chemical compound CCCCN1CC1 XIEJPTDTTYFCJM-UHFFFAOYSA-N 0.000 description 1
- LBTUZIHPJOSGFS-UHFFFAOYSA-N 1-decylaziridine Chemical compound CCCCCCCCCCN1CC1 LBTUZIHPJOSGFS-UHFFFAOYSA-N 0.000 description 1
- VTHSQZWBQSWDHD-UHFFFAOYSA-N 1-dodecylaziridine Chemical compound CCCCCCCCCCCCN1CC1 VTHSQZWBQSWDHD-UHFFFAOYSA-N 0.000 description 1
- LUNWJKXZDYXTDB-UHFFFAOYSA-N 1-ethyl-2,3-dimethylaziridine Chemical compound CCN1C(C)C1C LUNWJKXZDYXTDB-UHFFFAOYSA-N 0.000 description 1
- UJGVUACWGCQEAO-UHFFFAOYSA-N 1-ethylaziridine Chemical compound CCN1CC1 UJGVUACWGCQEAO-UHFFFAOYSA-N 0.000 description 1
- AKNYMGBMJIDSQQ-UHFFFAOYSA-N 1-hexylaziridine Chemical compound CCCCCCN1CC1 AKNYMGBMJIDSQQ-UHFFFAOYSA-N 0.000 description 1
- GGAYGPXRUVKNBK-UHFFFAOYSA-N 1-methyl-2-pentylaziridine Chemical compound CCCCCC1CN1C GGAYGPXRUVKNBK-UHFFFAOYSA-N 0.000 description 1
- NTWLTKMOHDXNCK-UHFFFAOYSA-N 1-methyl-2-phenylaziridine Chemical compound CN1CC1C1=CC=CC=C1 NTWLTKMOHDXNCK-UHFFFAOYSA-N 0.000 description 1
- XLJQPXVBQNJNLW-UHFFFAOYSA-N 1-methylaziridine Chemical compound CN1CC1 XLJQPXVBQNJNLW-UHFFFAOYSA-N 0.000 description 1
- OFGUDXIHTSHDIV-UHFFFAOYSA-N 1-methylaziridine-2-carbonitrile Chemical compound CN1CC1C#N OFGUDXIHTSHDIV-UHFFFAOYSA-N 0.000 description 1
- PZTZZKUYPINOIO-UHFFFAOYSA-N 1-nonylaziridine Chemical compound CCCCCCCCCN1CC1 PZTZZKUYPINOIO-UHFFFAOYSA-N 0.000 description 1
- ZPUJFEMAHSZIJA-UHFFFAOYSA-N 1-octylaziridine Chemical compound CCCCCCCCN1CC1 ZPUJFEMAHSZIJA-UHFFFAOYSA-N 0.000 description 1
- BCOPEHCVRGBNBQ-UHFFFAOYSA-N 1-pentan-2-ylaziridine Chemical compound CCCC(C)N1CC1 BCOPEHCVRGBNBQ-UHFFFAOYSA-N 0.000 description 1
- CGZJJNOOVORRPG-UHFFFAOYSA-N 1-pentan-3-ylaziridine Chemical compound CCC(CC)N1CC1 CGZJJNOOVORRPG-UHFFFAOYSA-N 0.000 description 1
- HVORHUUJKHPQQA-UHFFFAOYSA-N 1-pentylaziridine Chemical compound CCCCCN1CC1 HVORHUUJKHPQQA-UHFFFAOYSA-N 0.000 description 1
- MMMPMWQSPXSMAH-UHFFFAOYSA-N 1-propan-2-ylaziridine Chemical compound CC(C)N1CC1 MMMPMWQSPXSMAH-UHFFFAOYSA-N 0.000 description 1
- APKJRCRGAMSYHH-UHFFFAOYSA-N 1-propylaziridine Chemical compound CCCN1CC1 APKJRCRGAMSYHH-UHFFFAOYSA-N 0.000 description 1
- BBFCEQFUUOTJPD-UHFFFAOYSA-N 1-tert-butylaziridine Chemical compound CC(C)(C)N1CC1 BBFCEQFUUOTJPD-UHFFFAOYSA-N 0.000 description 1
- LGCXTJVESOYSTD-UHFFFAOYSA-N 1-tetradecylaziridine Chemical compound CCCCCCCCCCCCCCN1CC1 LGCXTJVESOYSTD-UHFFFAOYSA-N 0.000 description 1
- WLYQAIJKUUYCKF-UHFFFAOYSA-N 1-undecylaziridine Chemical compound CCCCCCCCCCCN1CC1 WLYQAIJKUUYCKF-UHFFFAOYSA-N 0.000 description 1
- NLOCPTKNDBXYOE-UHFFFAOYSA-N 2,2-dimethyl-1-propylaziridine Chemical compound CCCN1CC1(C)C NLOCPTKNDBXYOE-UHFFFAOYSA-N 0.000 description 1
- WZKIMACENGPRTO-UHFFFAOYSA-N 2-(3-chloropropyl)-1-methylaziridine Chemical compound CN1CC1CCCCl WZKIMACENGPRTO-UHFFFAOYSA-N 0.000 description 1
- JDXYUTWNVLYVBQ-UHFFFAOYSA-N 2-ethyl-1,3-dimethylaziridine Chemical compound CCC1C(C)N1C JDXYUTWNVLYVBQ-UHFFFAOYSA-N 0.000 description 1
- PJFNNMFXEVADGK-UHFFFAOYSA-N 2-hydroxy-n-phenylacetamide Chemical compound OCC(=O)NC1=CC=CC=C1 PJFNNMFXEVADGK-UHFFFAOYSA-N 0.000 description 1
- JLUVYNNUSJOSKB-UHFFFAOYSA-N 2-methyl-1-propan-2-ylaziridine Chemical compound CC(C)N1CC1C JLUVYNNUSJOSKB-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- ILXZCROTAHXUBF-UHFFFAOYSA-N 6-methyl-6-azabicyclo[3.1.0]hexane Chemical compound C1CCC2N(C)C21 ILXZCROTAHXUBF-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- NBYJNZPVUMXXNZ-UHFFFAOYSA-N butyl 3-(aziridin-1-yl)-2-methylpropanoate Chemical compound CCCCOC(=O)C(C)CN1CC1 NBYJNZPVUMXXNZ-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical group CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- IKMSGGHCWBSOOO-UHFFFAOYSA-N methyl 3-(aziridin-1-yl)propanoate Chemical compound COC(=O)CCN1CC1 IKMSGGHCWBSOOO-UHFFFAOYSA-N 0.000 description 1
- OWMCBRQWBVLBFQ-UHFFFAOYSA-N methyl 4-(aziridin-1-yl)butanoate Chemical compound COC(=O)CCCN1CC1 OWMCBRQWBVLBFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- GQGNHELPXHFFPK-UHFFFAOYSA-N n-(2-chloroethyl)-n-decylsulfamoyl chloride Chemical compound CCCCCCCCCCN(S(Cl)(=O)=O)CCCl GQGNHELPXHFFPK-UHFFFAOYSA-N 0.000 description 1
- WPVYUVMMYHXFSO-UHFFFAOYSA-N n-(2-chloroethyl)-n-ethylsulfamoyl chloride Chemical compound CCN(S(Cl)(=O)=O)CCCl WPVYUVMMYHXFSO-UHFFFAOYSA-N 0.000 description 1
- VBYIHIHYSILDBB-UHFFFAOYSA-N n-(2-chloroethyl)-n-hexylsulfamoyl chloride Chemical compound CCCCCCN(S(Cl)(=O)=O)CCCl VBYIHIHYSILDBB-UHFFFAOYSA-N 0.000 description 1
- BNMDKFLVWRQKCU-UHFFFAOYSA-N n-(2-chloroethyl)-n-methylsulfamoyl chloride Chemical compound ClS(=O)(=O)N(C)CCCl BNMDKFLVWRQKCU-UHFFFAOYSA-N 0.000 description 1
- NENFVRDXVOXMDC-UHFFFAOYSA-N n-(2-chloroethyl)-n-octylsulfamoyl chloride Chemical compound CCCCCCCCN(S(Cl)(=O)=O)CCCl NENFVRDXVOXMDC-UHFFFAOYSA-N 0.000 description 1
- YKEZOKIPIIBNDN-UHFFFAOYSA-N n-(2-chloroethyl)sulfamoyl chloride Chemical compound ClCCNS(Cl)(=O)=O YKEZOKIPIIBNDN-UHFFFAOYSA-N 0.000 description 1
- RWLSMSVIDUANNO-UHFFFAOYSA-N n-(2-chloroethyl)sulfamoyl fluoride Chemical compound FS(=O)(=O)NCCCl RWLSMSVIDUANNO-UHFFFAOYSA-N 0.000 description 1
- MIMFWMJURQJTMC-UHFFFAOYSA-N n-butyl-n-(2-chloroethyl)sulfamoyl chloride Chemical compound CCCCN(S(Cl)(=O)=O)CCCl MIMFWMJURQJTMC-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- PLXPTFQGYWXIEA-UHFFFAOYSA-N nitroformonitrile Chemical compound [O-][N+](=O)C#N PLXPTFQGYWXIEA-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
- C07C309/80—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a saturated carbon skeleton
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 |
|---|---|---|---|
| DE19742408530 DE2408530A1 (de) | 1974-02-22 | 1974-02-22 | Verfahren zur herstellung von betahalogenalkylaminosulfonylhalogeniden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50121224A JPS50121224A (enrdf_load_stackoverflow) | 1975-09-23 |
| JPS5833868B2 true JPS5833868B2 (ja) | 1983-07-22 |
Family
ID=5908156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50021073A Expired JPS5833868B2 (ja) | 1974-02-22 | 1975-02-21 | ベ−タ − ハロゲンアルキルアミノスルホニルハロゲニドノ セイホウ |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2963400D1 (en) * | 1978-07-01 | 1982-09-16 | Basf Ag | Sulphamic acid halides and method for their preparation |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| PL374371A1 (en) | 2002-05-16 | 2005-10-17 | Basf Aktiengesellschaft | Method for the production of sulphamic acid halogenides |
-
1974
- 1974-02-22 DE DE19742408530 patent/DE2408530A1/de active Granted
-
1975
- 1975-02-12 IL IL46625A patent/IL46625A/xx unknown
- 1975-02-12 IT IT20214/75A patent/IT1031697B/it active
- 1975-02-14 BE BE153351A patent/BE825526A/xx not_active IP Right Cessation
- 1975-02-20 DD DD184314A patent/DD119581A5/xx unknown
- 1975-02-20 NL NLAANVRAGE7502035,A patent/NL178072C/xx not_active IP Right Cessation
- 1975-02-20 SU SU752108280A patent/SU604483A3/ru active
- 1975-02-20 HU HU75BA00003214A patent/HU171858B/hu unknown
- 1975-02-21 FR FR7505461A patent/FR2262028B2/fr not_active Expired
- 1975-02-21 JP JP50021073A patent/JPS5833868B2/ja not_active Expired
- 1975-02-21 CH CH218275A patent/CH586668A5/xx not_active IP Right Cessation
- 1975-02-21 GB GB7304/75A patent/GB1488186A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH586668A5 (enrdf_load_stackoverflow) | 1977-04-15 |
| IL46625A0 (en) | 1975-04-25 |
| HU171858B (hu) | 1978-04-28 |
| BE825526A (fr) | 1975-08-14 |
| IT1031697B (it) | 1979-05-10 |
| NL178072B (nl) | 1985-08-16 |
| IL46625A (en) | 1978-08-31 |
| FR2262028A2 (enrdf_load_stackoverflow) | 1975-09-19 |
| DE2408530C2 (enrdf_load_stackoverflow) | 1987-07-09 |
| JPS50121224A (enrdf_load_stackoverflow) | 1975-09-23 |
| NL7502035A (nl) | 1975-08-26 |
| NL178072C (nl) | 1986-01-16 |
| FR2262028B2 (enrdf_load_stackoverflow) | 1978-04-07 |
| GB1488186A (en) | 1977-10-05 |
| DE2408530A1 (de) | 1975-09-04 |
| SU604483A3 (ru) | 1978-04-25 |
| DD119581A5 (enrdf_load_stackoverflow) | 1976-05-05 |
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