NO123529B - Fremgangsmate ved fremstilling av 1-substituerte 5-nitroimidazol-2-ylalkyl-carbamater - Google Patents
Fremgangsmate ved fremstilling av 1-substituerte 5-nitroimidazol-2-ylalkyl-carbamater Download PDFInfo
- Publication number
- NO123529B NO123529B NO163799A NO16379966A NO123529B NO 123529 B NO123529 B NO 123529B NO 163799 A NO163799 A NO 163799A NO 16379966 A NO16379966 A NO 16379966A NO 123529 B NO123529 B NO 123529B
- Authority
- NO
- Norway
- Prior art keywords
- nitroimidazole
- methyl
- nitroimidazol
- solution
- added
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 55
- 238000002360 preparation method Methods 0.000 title claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title description 8
- -1 carbonyl halide Chemical class 0.000 claims description 48
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 7
- JSAQDPJIVQMBAY-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methanol Chemical compound CN1C(CO)=NC=C1[N+]([O-])=O JSAQDPJIVQMBAY-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- XWIYNNJPQAWSGT-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methylcarbamic acid Chemical compound CN1C(CNC(O)=O)=NC=C1[N+]([O-])=O XWIYNNJPQAWSGT-UHFFFAOYSA-N 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- ICUHNDFYVMGWSQ-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methanol phenyl hydrogen carbonate Chemical compound C(OC1=CC=CC=C1)(O)=O.CN1C(=NC=C1[N+](=O)[O-])CO ICUHNDFYVMGWSQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 55
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- 239000000203 mixture Substances 0.000 description 43
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- 230000008018 melting Effects 0.000 description 39
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- 238000001914 filtration Methods 0.000 description 21
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- 239000002904 solvent Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
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- 239000002244 precipitate Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
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- 239000007787 solid Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
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- ZWUJTBSXSRTFCC-UHFFFAOYSA-N 2-(5-nitroimidazol-1-yl)acetic acid Chemical compound OC(=O)CN1C=NC=C1[N+]([O-])=O ZWUJTBSXSRTFCC-UHFFFAOYSA-N 0.000 description 6
- VYDWQPKRHOGLPA-UHFFFAOYSA-N 5-nitroimidazole Chemical compound [O-][N+](=O)C1=CN=CN1 VYDWQPKRHOGLPA-UHFFFAOYSA-N 0.000 description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- KLQMSCYASYAWMG-UHFFFAOYSA-N 1-(1-methyl-5-nitroimidazol-2-yl)ethanol Chemical compound CC(O)C1=NC=C([N+]([O-])=O)N1C KLQMSCYASYAWMG-UHFFFAOYSA-N 0.000 description 5
- JLQLFVSTEDRFAD-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbaldehyde Chemical compound CN1C(C=O)=NC=C1[N+]([O-])=O JLQLFVSTEDRFAD-UHFFFAOYSA-N 0.000 description 5
- DFMZECOLZRIPOT-UHFFFAOYSA-N 2-(5-nitroimidazol-1-yl)ethanol Chemical compound OCCN1C=NC=C1[N+]([O-])=O DFMZECOLZRIPOT-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
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- 230000015572 biosynthetic process Effects 0.000 description 4
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- KOSYAAIZOGNATQ-UHFFFAOYSA-N o-phenyl chloromethanethioate Chemical compound ClC(=S)OC1=CC=CC=C1 KOSYAAIZOGNATQ-UHFFFAOYSA-N 0.000 description 3
- YYPUSXWRDIQUQE-UHFFFAOYSA-N phenoxymethanethioic s-acid Chemical class OC(=S)OC1=CC=CC=C1 YYPUSXWRDIQUQE-UHFFFAOYSA-N 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
- KNVMOFUTOGRUBR-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)N(C)C(C(=O)C=2C=CC=CC=2)=N1 KNVMOFUTOGRUBR-UHFFFAOYSA-N 0.000 description 2
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- IZLUUNDLPUWQEK-UHFFFAOYSA-N 2-(5-nitroimidazol-1-yl)acetamide Chemical compound [N+](=O)([O-])C1=CN=CN1CC(=O)N IZLUUNDLPUWQEK-UHFFFAOYSA-N 0.000 description 2
- XEVAOOVNFDMYQX-UHFFFAOYSA-N 2-(5-nitroimidazol-1-yl)acetonitrile Chemical compound [O-][N+](=O)C1=CN=CN1CC#N XEVAOOVNFDMYQX-UHFFFAOYSA-N 0.000 description 2
- AKVGRVXEDNPSLB-UHFFFAOYSA-N 2-(5-nitroimidazol-1-yl)acetonitrile hydrochloride Chemical compound Cl.[N+](=O)([O-])C1=CN=CN1CC#N AKVGRVXEDNPSLB-UHFFFAOYSA-N 0.000 description 2
- JHJNVLHKDDFEOI-UHFFFAOYSA-N 2-(5-nitroimidazol-1-yl)propanoic acid Chemical compound OC(=O)C(C)N1C=NC=C1[N+]([O-])=O JHJNVLHKDDFEOI-UHFFFAOYSA-N 0.000 description 2
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- IFELUMYGWLOMEA-UHFFFAOYSA-N 2-benzyl-1-methyl-5-nitroimidazole Chemical compound CN1C(=NC=C1[N+](=O)[O-])CC1=CC=CC=C1 IFELUMYGWLOMEA-UHFFFAOYSA-N 0.000 description 2
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- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- JULQODDWZXFMFB-UHFFFAOYSA-N 1-(5-nitroimidazol-1-yl)pentan-2-ol Chemical compound OC(CN1C=NC=C1[N+](=O)[O-])CCC JULQODDWZXFMFB-UHFFFAOYSA-N 0.000 description 1
- VZCDYFPVDNHALT-UHFFFAOYSA-N 1-(5-nitroimidazol-1-yl)pentan-2-yl acetate Chemical compound C(C)(=O)OC(CN1C=NC=C1[N+](=O)[O-])CCC VZCDYFPVDNHALT-UHFFFAOYSA-N 0.000 description 1
- AIPJFIRBMBEDLL-UHFFFAOYSA-N 1-(5-nitroimidazol-1-yl)pentan-3-one Chemical compound O=C(CCN1C=NC=C1[N+](=O)[O-])CC AIPJFIRBMBEDLL-UHFFFAOYSA-N 0.000 description 1
- HBEULAOGTOICGX-UHFFFAOYSA-N 1-(5-nitroimidazol-1-yl)propan-2-ol Chemical compound CC(O)CN1C=NC=C1[N+]([O-])=O HBEULAOGTOICGX-UHFFFAOYSA-N 0.000 description 1
- RVCAAXNKBAODSK-UHFFFAOYSA-N 1-(5-nitroimidazol-1-yl)propan-2-yl acetate Chemical compound C(C)(=O)OC(CN1C=NC=C1[N+](=O)[O-])C RVCAAXNKBAODSK-UHFFFAOYSA-N 0.000 description 1
- BZWJDKJBAVXCMH-UHFFFAOYSA-N 1-diazopropane Chemical compound CCC=[N+]=[N-] BZWJDKJBAVXCMH-UHFFFAOYSA-N 0.000 description 1
- PNTWOGNQWJAKGA-UHFFFAOYSA-N 2-(1-methyl-5-nitroimidazol-2-yl)propane-1,3-diol Chemical compound CN1C(C(CO)CO)=NC=C1[N+]([O-])=O PNTWOGNQWJAKGA-UHFFFAOYSA-N 0.000 description 1
- KYMBXDBZIASVNV-UHFFFAOYSA-N 2-(5-nitroimidazol-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1C=NC=C1[N+]([O-])=O KYMBXDBZIASVNV-UHFFFAOYSA-N 0.000 description 1
- MMTRWRWIGSMZQW-UHFFFAOYSA-N 2-(5-nitroimidazol-1-yl)propanenitrile Chemical compound [N+](=O)([O-])C1=CN=CN1C(C#N)C MMTRWRWIGSMZQW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NAPDOWNULRULLI-UHFFFAOYSA-N 2-benzyl-1h-imidazole Chemical compound C=1C=CC=CC=1CC1=NC=CN1 NAPDOWNULRULLI-UHFFFAOYSA-N 0.000 description 1
- OOHUVYRBDVZSIE-UHFFFAOYSA-N 2-diazo-4-phenylbutanoic acid Chemical compound OC(=O)C(CCc1ccccc1)=[N+]=[N-] OOHUVYRBDVZSIE-UHFFFAOYSA-N 0.000 description 1
- MIVRMHJOEYRXQB-UHFFFAOYSA-N 2-diazonio-1-methoxyethenolate Chemical compound COC(=O)C=[N+]=[N-] MIVRMHJOEYRXQB-UHFFFAOYSA-N 0.000 description 1
- KSKYFYIEWBCMDT-UHFFFAOYSA-N 2-diazonio-1-methoxyprop-1-en-1-olate Chemical compound COC(=O)C(C)=[N+]=[N-] KSKYFYIEWBCMDT-UHFFFAOYSA-N 0.000 description 1
- JBBKWIFIXPBQGZ-UHFFFAOYSA-N 2-diazonio-1-phenylmethoxyethenolate Chemical compound [N-]=[N+]=CC(=O)OCC1=CC=CC=C1 JBBKWIFIXPBQGZ-UHFFFAOYSA-N 0.000 description 1
- KPTZIQYZCKOZFH-UHFFFAOYSA-N 2-diazonio-1-propoxyethenolate Chemical compound CCCOC(=O)C=[N+]=[N-] KPTZIQYZCKOZFH-UHFFFAOYSA-N 0.000 description 1
- IKHWMIDJCAVLAK-UHFFFAOYSA-N 2-diazopropanoic acid Chemical compound [N+](=[N-])=C(C(=O)O)C IKHWMIDJCAVLAK-UHFFFAOYSA-N 0.000 description 1
- GDHROTCPZLVPJT-UHFFFAOYSA-N 2-ethyloxetane Chemical compound CCC1CCO1 GDHROTCPZLVPJT-UHFFFAOYSA-N 0.000 description 1
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
- FUCSWGRAIIZMAB-UHFFFAOYSA-N 2-oxoethyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=O)C1=CC=CC=C1 FUCSWGRAIIZMAB-UHFFFAOYSA-N 0.000 description 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
- NIWONKJNKKTBJE-UHFFFAOYSA-N 3-(1-methyl-5-nitroimidazol-2-yl)prop-2-en-1-ol Chemical compound CN1C(C=CCO)=NC=C1[N+]([O-])=O NIWONKJNKKTBJE-UHFFFAOYSA-N 0.000 description 1
- NAIWRVCAUSBYFO-UHFFFAOYSA-N 3-(5-nitroimidazol-1-yl)propyl acetate Chemical compound C(C)(=O)OCCCN1C=NC=C1[N+](=O)[O-] NAIWRVCAUSBYFO-UHFFFAOYSA-N 0.000 description 1
- GDGNUJMEAHSQEU-UHFFFAOYSA-N 4-(5-nitroimidazol-1-yl)butan-2-one Chemical compound O=C(CCN1C=NC=C1[N+](=O)[O-])C GDGNUJMEAHSQEU-UHFFFAOYSA-N 0.000 description 1
- CASPDYMGDTZHSO-UHFFFAOYSA-N 4-(5-nitroimidazol-1-yl)butan-2-yl acetate Chemical compound C(C)(=O)OC(CCN1C=NC=C1[N+](=O)[O-])C CASPDYMGDTZHSO-UHFFFAOYSA-N 0.000 description 1
- FXCYUKOCJPFBOH-UHFFFAOYSA-N 5-nitro-1-propylimidazole Chemical compound CCCN1C=NC=C1[N+]([O-])=O FXCYUKOCJPFBOH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- SNDXYDCSPYUCEZ-UHFFFAOYSA-N CCCCC(C)(C(O)=O)N1C([N+]([O-])=O)=CN=C1 Chemical compound CCCCC(C)(C(O)=O)N1C([N+]([O-])=O)=CN=C1 SNDXYDCSPYUCEZ-UHFFFAOYSA-N 0.000 description 1
- UWJGPLGCYLYOCS-UHFFFAOYSA-N CN1C([N+]([O-])=O)=CN=C1CN(C(O)=O)N Chemical compound CN1C([N+]([O-])=O)=CN=C1CN(C(O)=O)N UWJGPLGCYLYOCS-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 description 1
- OIMSBIGZROGINA-UHFFFAOYSA-N OC(CN1C=NC=C1[N+](=O)[O-])CC Chemical compound OC(CN1C=NC=C1[N+](=O)[O-])CC OIMSBIGZROGINA-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 208000005448 Trichomonas Infections Diseases 0.000 description 1
- 206010044620 Trichomoniasis Diseases 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- FVFZQFLJXZMSGB-UHFFFAOYSA-N [N+](=O)([O-])C1=CN=CN1C(C(=O)N)C Chemical compound [N+](=O)([O-])C1=CN=CN1C(C(=O)N)C FVFZQFLJXZMSGB-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- CRGRWBQSZSQVIE-UHFFFAOYSA-N diazomethylbenzene Chemical compound [N-]=[N+]=CC1=CC=CC=C1 CRGRWBQSZSQVIE-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- GQZLUBQHOLNJIL-UHFFFAOYSA-N diphenoxymethanethione Chemical compound C=1C=CC=CC=1OC(=S)OC1=CC=CC=C1 GQZLUBQHOLNJIL-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HFTNNOZFRQLFQB-UHFFFAOYSA-N ethenoxy(trimethyl)silane Chemical compound C[Si](C)(C)OC=C HFTNNOZFRQLFQB-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 201000002311 trypanosomiasis Diseases 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07D233/66—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 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 to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47019065A | 1965-07-07 | 1965-07-07 | |
| US55092566A | 1966-05-18 | 1966-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123529B true NO123529B (no) | 1971-12-06 |
Family
ID=27043000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO163799A NO123529B (no) | 1965-07-07 | 1966-07-06 | Fremgangsmate ved fremstilling av 1-substituerte 5-nitroimidazol-2-ylalkyl-carbamater |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3458528A (pt) |
| BE (1) | BE683795A (pt) |
| BR (1) | BR6681061D0 (pt) |
| CH (1) | CH498125A (pt) |
| DE (1) | DE1620019A1 (pt) |
| DK (1) | DK139198B (pt) |
| ES (1) | ES329174A1 (pt) |
| FI (1) | FI46071C (pt) |
| GB (1) | GB1153346A (pt) |
| IL (1) | IL25952A (pt) |
| NL (1) | NL6609553A (pt) |
| NO (1) | NO123529B (pt) |
| SE (1) | SE328298B (pt) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670916A1 (de) * | 1967-08-29 | 1971-04-08 | Bayer Ag | Verfahren zur Herstellung neuartiger Carbamidsaeureester |
| FR2054504B1 (pt) * | 1969-07-18 | 1973-06-08 | Rhone Poulenc Sa | |
| US3987053A (en) * | 1971-07-30 | 1976-10-19 | Gruppo Lepetit S.P.A. | 2-nitroimidazol derivatives |
| GB1408367A (en) * | 1972-07-03 | 1975-10-01 | Searle & Co | 2- 2-methyl-5-nitro-1-imidazolyl ethyl dithiocarbamates |
| US3976778A (en) * | 1973-08-13 | 1976-08-24 | Ciba-Geigy Corporation | Imidazoles and processes for their production |
| GB1542840A (en) * | 1975-02-03 | 1979-03-28 | Smith Kline French Lab | Heterocyclic dithiocarbamates and isothioureas |
| GB1526451A (en) * | 1976-01-27 | 1978-09-27 | Lepetit Spa | Alpha,alpha,1-trimethyl-2-nitroimidazole-5-methanol derivatives |
| DE2827351A1 (de) * | 1978-06-22 | 1980-01-10 | Basf Ag | 2-substituierte 1-alykl-nitroimidazole und verfahren zur herstellung von 2-substituierten 1-alkyl-nitroimidazolen |
| AU2017333782A1 (en) | 2016-09-29 | 2019-03-28 | Bayer Aktiengesellschaft | Novel 5-substituted imidazolylmethyl derivatives |
| CN109553580B (zh) * | 2017-09-25 | 2023-08-11 | 南京长澳医药科技有限公司 | 硝基咪唑类化合物中间体及其盐的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2944061A (en) * | 1957-09-20 | 1960-07-05 | Acyl derivatives and process | |
| US3104256A (en) * | 1962-03-01 | 1963-09-17 | American Home Prod | Alicyclic carbamate and its preparation |
| US3224862A (en) * | 1962-04-02 | 1965-12-21 | Monsanto Co | Controlling vegetation with phenylthionocarbamates |
| US3252986A (en) * | 1963-11-07 | 1966-05-24 | American Cyanamid Co | 2-carbethoxyaminobenzamides |
-
1966
- 1966-05-18 US US550925A patent/US3458528A/en not_active Expired - Lifetime
- 1966-06-12 IL IL25952A patent/IL25952A/xx unknown
- 1966-07-04 GB GB29844/66A patent/GB1153346A/en not_active Expired
- 1966-07-05 FI FI661795A patent/FI46071C/fi active
- 1966-07-06 NO NO163799A patent/NO123529B/no unknown
- 1966-07-06 ES ES0329174A patent/ES329174A1/es not_active Expired
- 1966-07-06 DK DK348966AA patent/DK139198B/da unknown
- 1966-07-06 DE DE19661620019 patent/DE1620019A1/de active Pending
- 1966-07-06 SE SE09273/66A patent/SE328298B/xx unknown
- 1966-07-06 BR BR181061/66A patent/BR6681061D0/pt unknown
- 1966-07-07 NL NL6609553A patent/NL6609553A/xx unknown
- 1966-07-07 BE BE683795D patent/BE683795A/xx unknown
- 1966-07-07 CH CH988766A patent/CH498125A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620019A1 (de) | 1970-03-26 |
| DK139198B (da) | 1979-01-08 |
| NL6609553A (pt) | 1967-01-09 |
| GB1153346A (en) | 1969-05-29 |
| FI46071C (fi) | 1972-12-11 |
| SE328298B (pt) | 1970-09-14 |
| FI46071B (pt) | 1972-08-31 |
| ES329174A1 (es) | 1967-05-01 |
| CH498125A (de) | 1970-10-31 |
| BR6681061D0 (pt) | 1973-12-26 |
| DK139198C (pt) | 1979-07-09 |
| US3458528A (en) | 1969-07-29 |
| IL25952A (en) | 1970-11-30 |
| BE683795A (pt) | 1967-01-09 |
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