DD147846A5 - Verfahren zur herstellung von 2-arylaminohexahydropyrimidinen und-imidazolinen - Google Patents
Verfahren zur herstellung von 2-arylaminohexahydropyrimidinen und-imidazolinen Download PDFInfo
- Publication number
- DD147846A5 DD147846A5 DD78217704A DD21770478A DD147846A5 DD 147846 A5 DD147846 A5 DD 147846A5 DD 78217704 A DD78217704 A DD 78217704A DD 21770478 A DD21770478 A DD 21770478A DD 147846 A5 DD147846 A5 DD 147846A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- carbon atoms
- groups
- general formula
- alkyl
- compounds
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 18
- 150000002462 imidazolines Chemical class 0.000 title abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 49
- -1 benzyloxy, benzylthio, phenoxy Chemical group 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 13
- 125000002252 acyl group Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000000536 complexating effect Effects 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 3
- 101100072621 Streptomyces griseus ind7 gene Proteins 0.000 abstract 1
- 238000003898 horticulture Methods 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- 230000008018 melting Effects 0.000 description 40
- 238000002844 melting Methods 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PEHDFSFYZKSKGH-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound NC1=NCCCN1 PEHDFSFYZKSKGH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 4
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical compound NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- OKOVDKPGUFVBLG-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound C1CCCCC1C1=CC=C(N=C2NCCCN2)C=C1 OKOVDKPGUFVBLG-UHFFFAOYSA-N 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ILSPCYPUJFVVLN-UHFFFAOYSA-N C(CCC)SC1=CC=C(C=C1)C1NCC(N1)=N Chemical compound C(CCC)SC1=CC=C(C=C1)C1NCC(N1)=N ILSPCYPUJFVVLN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- DNWWODFFEFZASF-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1NC1=CC=C(C2CCCCC2)C=C1 DNWWODFFEFZASF-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- CVTFZKSIFLQDJI-UHFFFAOYSA-N 2-(1,3-diazinan-2-yl)acetic acid Chemical compound OC(=O)CC1NCCCN1 CVTFZKSIFLQDJI-UHFFFAOYSA-N 0.000 description 2
- ZZQTTWKFWWDCED-UHFFFAOYSA-N C1CCC(CC1)C2=CC=C(C=C2)N3CCN=C3N Chemical compound C1CCC(CC1)C2=CC=C(C=C2)N3CCN=C3N ZZQTTWKFWWDCED-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 241000221577 Uromyces appendiculatus Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 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 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 150000002461 imidazolidines Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- JCOPITWIWLFFPC-UHFFFAOYSA-N n-phenyl-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1NC1=CC=CC=C1 JCOPITWIWLFFPC-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PXVPXJHMTUKENZ-UHFFFAOYSA-N 1-butyl-4-isothiocyanatobenzene Chemical compound CCCCC1=CC=C(N=C=S)C=C1 PXVPXJHMTUKENZ-UHFFFAOYSA-N 0.000 description 1
- BAXHEOKDDCCGEM-UHFFFAOYSA-N 1-cyclohexyl-4-isocyanobenzene Chemical compound C1=CC([N+]#[C-])=CC=C1C1CCCCC1 BAXHEOKDDCCGEM-UHFFFAOYSA-N 0.000 description 1
- AHEKENQPEQYCMG-UHFFFAOYSA-N 1-methyl-1,3-diazinane Chemical compound CN1CCCNC1 AHEKENQPEQYCMG-UHFFFAOYSA-N 0.000 description 1
- QRTNOTXNTUWFPJ-UHFFFAOYSA-N 1-phenyl-5,6-dihydro-4H-pyrimidin-2-amine Chemical compound C1CN=C(N(C1)C2=CC=CC=C2)N QRTNOTXNTUWFPJ-UHFFFAOYSA-N 0.000 description 1
- HTWYCTFASPHKJG-UHFFFAOYSA-N 2-(4-butylphenyl)-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound C(CCC)C1=CC=C(C=C1)C1NCCC(N1)=N HTWYCTFASPHKJG-UHFFFAOYSA-N 0.000 description 1
- HHOLCPIURHHFNR-UHFFFAOYSA-N 2-(4-heptylphenyl)-2,5-dihydro-1H-imidazol-4-amine Chemical compound C(CCCCCC)C1=CC=C(C=C1)C1NCC(N1)=N HHOLCPIURHHFNR-UHFFFAOYSA-N 0.000 description 1
- CUUDMFVANGJFGA-UHFFFAOYSA-N 2-(4-hexoxyphenyl)-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound C(CCCCC)OC1=CC=C(C=C1)C1NCCC(N1)=N CUUDMFVANGJFGA-UHFFFAOYSA-N 0.000 description 1
- SKKXCFRUMVWLCI-UHFFFAOYSA-N 2-(4-hexylphenyl)-2,5-dihydro-1H-imidazol-4-amine Chemical compound C(CCCCC)C1=CC=C(C=C1)C1NCC(N1)=N SKKXCFRUMVWLCI-UHFFFAOYSA-N 0.000 description 1
- AVULWYWLJJFVBB-UHFFFAOYSA-N 2-(4-octoxyphenyl)-1,2,5,6-tetrahydropyrimidin-4-amine Chemical compound C(CCCCCCC)OC1=CC=C(C=C1)C1NCCC(N1)=N AVULWYWLJJFVBB-UHFFFAOYSA-N 0.000 description 1
- XSJDIGYQRHMGMM-UHFFFAOYSA-N 2-(4-octylphenyl)-2,5-dihydro-1H-imidazol-4-amine Chemical compound C(CCCCCCC)C1=CC=C(C=C1)C1NCC(N1)=N XSJDIGYQRHMGMM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- VWZXCKKMXLQTFF-UHFFFAOYSA-N 2-butylsulfanylimidazolidine;hydrobromide Chemical compound Br.CCCCSC1NCCN1 VWZXCKKMXLQTFF-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- JLNMBIKJQAKQBH-UHFFFAOYSA-N 4-cyclohexylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCC1 JLNMBIKJQAKQBH-UHFFFAOYSA-N 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FRQGDZPERKMXNA-UHFFFAOYSA-N 4-n-(4,5-dihydro-1h-imidazol-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical group N1CCN=C1NC(C=C1)=CC=C1NC1=CC=CC=C1 FRQGDZPERKMXNA-UHFFFAOYSA-N 0.000 description 1
- OULQIRTYSJHFKP-UHFFFAOYSA-N 4h-imidazol-5-amine Chemical compound N=C1CNC=N1 OULQIRTYSJHFKP-UHFFFAOYSA-N 0.000 description 1
- FXCZIQLITKAYEO-UHFFFAOYSA-N 6-methyl-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound CC1CCNC(N)=N1 FXCZIQLITKAYEO-UHFFFAOYSA-N 0.000 description 1
- GUWKSWBBEJWXKH-UHFFFAOYSA-N C(CC(C)C)C=1C=C(SC1)C1NCCC(N1)=N Chemical compound C(CC(C)C)C=1C=C(SC1)C1NCCC(N1)=N GUWKSWBBEJWXKH-UHFFFAOYSA-N 0.000 description 1
- YZSHRMPCYBRKQU-UHFFFAOYSA-N C(CCC)C1=CC=C(C=C1)C1NCC(N1)=N Chemical compound C(CCC)C1=CC=C(C=C1)C1NCC(N1)=N YZSHRMPCYBRKQU-UHFFFAOYSA-N 0.000 description 1
- RPSKYLBBPNSUDV-UHFFFAOYSA-N C1(CCCCC1)C1=CC=C(C=C1)C1NCC(C(N1)C)=N Chemical class C1(CCCCC1)C1=CC=C(C=C1)C1NCC(C(N1)C)=N RPSKYLBBPNSUDV-UHFFFAOYSA-N 0.000 description 1
- YNBWFHSNYXTDAQ-UHFFFAOYSA-N C1CNC(N=C1N)C2=CC3=CC=CC=C3C=C2 Chemical compound C1CNC(N=C1N)C2=CC3=CC=CC=C3C=C2 YNBWFHSNYXTDAQ-UHFFFAOYSA-N 0.000 description 1
- ONBPBPNEDFSQAA-UHFFFAOYSA-N CCCCC1=CC=C(C=C1)C2N=C(CCN2C)N Chemical compound CCCCC1=CC=C(C=C1)C2N=C(CCN2C)N ONBPBPNEDFSQAA-UHFFFAOYSA-N 0.000 description 1
- NPJKWZHDBMJXLR-UHFFFAOYSA-N CCCCCCC1=CSC(=C1)C2NCCC(=N2)N Chemical compound CCCCCCC1=CSC(=C1)C2NCCC(=N2)N NPJKWZHDBMJXLR-UHFFFAOYSA-N 0.000 description 1
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 1
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
- SPTHOEKISABNFX-UHFFFAOYSA-N OC(=S)S=N Chemical compound OC(=S)S=N SPTHOEKISABNFX-UHFFFAOYSA-N 0.000 description 1
- XTLGPJLVHVUKOU-UHFFFAOYSA-N S(=O)(=O)(O)O.C1(CCCCC1)C1=CC=C(C=C1)C1NCCC(N1)=N Chemical compound S(=O)(=O)(O)O.C1(CCCCC1)C1=CC=C(C=C1)C1NCCC(N1)=N XTLGPJLVHVUKOU-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- UVFZJMCAXJRLBB-UHFFFAOYSA-N hexyl 4-(4-amino-1,2,5,6-tetrahydropyrimidin-2-yl)benzoate Chemical compound C(CCCCC)OC(=O)C1=CC=C(C=C1)C1NCCC(N1)=N UVFZJMCAXJRLBB-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- SARIXARCHVWFBC-UHFFFAOYSA-N methyl n'-(4-cyclohexylphenyl)carbamimidothioate;hydroiodide Chemical compound I.C1=CC(NC(=N)SC)=CC=C1C1CCCCC1 SARIXARCHVWFBC-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CIYMQQLOODPCEE-UHFFFAOYSA-N n-(4-butylphenyl)-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound C1=CC(CCCC)=CC=C1N=C1NCCCN1 CIYMQQLOODPCEE-UHFFFAOYSA-N 0.000 description 1
- TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/14—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to said nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7711390A NL7711390A (nl) | 1977-10-18 | 1977-10-18 | Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD147846A5 true DD147846A5 (de) | 1981-04-22 |
Family
ID=19829358
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78208481A DD139989A5 (de) | 1977-10-18 | 1978-10-16 | Fungicidpraeparate |
| DD78217704A DD147846A5 (de) | 1977-10-18 | 1978-10-16 | Verfahren zur herstellung von 2-arylaminohexahydropyrimidinen und-imidazolinen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78208481A DD139989A5 (de) | 1977-10-18 | 1978-10-16 | Fungicidpraeparate |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4396617A (ko) |
| EP (1) | EP0001663B1 (ko) |
| JP (1) | JPS5463080A (ko) |
| AR (1) | AR225601A1 (ko) |
| AU (1) | AU521181B2 (ko) |
| CA (1) | CA1106845A (ko) |
| CS (2) | CS208757B2 (ko) |
| DD (2) | DD139989A5 (ko) |
| DE (1) | DE2861822D1 (ko) |
| DK (1) | DK458178A (ko) |
| EG (1) | EG13497A (ko) |
| ES (2) | ES474227A1 (ko) |
| HU (1) | HU178690B (ko) |
| IL (1) | IL55728A (ko) |
| IT (1) | IT1099744B (ko) |
| NL (1) | NL7711390A (ko) |
| NZ (1) | NZ188660A (ko) |
| PL (2) | PL120588B1 (ko) |
| SU (2) | SU895289A3 (ko) |
| TR (1) | TR20567A (ko) |
| ZA (1) | ZA785278B (ko) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7711390A (nl) * | 1977-10-18 | 1979-04-20 | Philips Nv | Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen. |
| US4321838A (en) * | 1979-08-13 | 1982-03-30 | Feldman Robert I | Power coupling for a chain saw |
| DE2933930A1 (de) * | 1979-08-22 | 1981-03-12 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-(2-chlor-4-cyclopropyl-phenylimino)-imidazolidin, dessen saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben. |
| US4647557A (en) * | 1982-12-28 | 1987-03-03 | Gerard Moinet | Novel heterocyclic derivatives bearing an amino radical, processes for their production and the pharmaceutical compositions containing them |
| US5292743A (en) * | 1989-10-10 | 1994-03-08 | Dowelanco | Fungicidal compositions, fungicidal compounds, their production and use |
| GB8922750D0 (en) * | 1989-10-10 | 1989-11-22 | Dow Chemical Co | Fungicidal compounds,their production and use |
| GB9016800D0 (en) * | 1990-07-31 | 1990-09-12 | Shell Int Research | Tetrahydropyrimidine derivatives |
| US5866579A (en) | 1997-04-11 | 1999-02-02 | Synaptic Pharmaceutical Corporation | Imidazole and imidazoline derivatives and uses thereof |
| NZ331480A (en) * | 1997-09-04 | 2000-02-28 | F | 2-(Arylphenyl)amino-imidazoline derivatives and pharmaceutical compositions |
| US6184242B1 (en) | 1997-09-04 | 2001-02-06 | Syntex Usa (Llc) | 2-(substituted-phenyl)amino-imidazoline derivatives |
| US6417186B1 (en) | 2000-11-14 | 2002-07-09 | Syntex (U.S.A.) Llc | Substituted-phenyl ketone derivatives as IP antagonists |
| BRPI0409957A (pt) * | 2003-05-01 | 2006-04-25 | Hoffmann La Roche | imidazolin-2-ilaminofenil amidas |
| CA2530538A1 (en) * | 2003-07-09 | 2005-01-20 | Keith Roger Bley | Thiophenylaminoimidazolines as prostaglandin i2 antagonists |
| JP2007308392A (ja) * | 2006-05-16 | 2007-11-29 | Bayer Cropscience Ag | 殺虫性ベンズアミジン類 |
| WO2016043260A1 (ja) * | 2014-09-19 | 2016-03-24 | 塩野義製薬株式会社 | 環状グアニジンまたはアミジン化合物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899426A (en) * | 1959-08-11 | Synthesis of l | ||
| US2899434A (en) * | 1959-08-11 | Z-phenylamino-l | ||
| FR1211341A (fr) * | 1955-12-19 | 1960-03-15 | A Wander Dr | Procédé pour la préparation de 2-amino-imidazolines |
| US3190802A (en) * | 1961-10-09 | 1965-06-22 | Boehringer Sohn Ingelheim | Shaving composition and method of using same |
| US3236857A (en) * | 1961-10-09 | 1966-02-22 | Boehringer Sohn Ingelheim | 2-(phenyl-amino)-1, 3-diazacyclopentene-(2) substitution products |
| BE632578A (ko) * | 1963-05-22 | |||
| DE1670274A1 (de) * | 1966-10-31 | 1970-07-16 | Boehringer Sohn Ingelheim | Neues Verfahren zur Herstellung von 2-Arylamino-1,3-diazacycloalkenen-(2) |
| US3882229A (en) * | 1972-07-21 | 1975-05-06 | Nordmark Werke Gmbh | Composition and method for shrinking mucous membranes |
| DE2316377C3 (de) * | 1973-04-02 | 1978-11-02 | Lentia Gmbh, Chem. U. Pharm. Erzeugnisse - Industriebedarf, 8000 Muenchen | Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen |
| AT330769B (de) * | 1974-04-05 | 1976-07-26 | Chemie Linz Ag | Verfahren zur herstellung von 2-arylamino- 2-imidazolin-derivaten und ihren salzen |
| DE2542702C2 (de) * | 1975-09-25 | 1983-11-10 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur Herstellung von 1-Benzoyl-2-(2,6-dichlorphenylamino)-2-imidazolin |
| NL7711390A (nl) * | 1977-10-18 | 1979-04-20 | Philips Nv | Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen. |
| US4262005A (en) * | 1978-05-31 | 1981-04-14 | The Boots Company Limited | Compounds, compositions and methods for controlling pests |
| DE2933930A1 (de) * | 1979-08-22 | 1981-03-12 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-(2-chlor-4-cyclopropyl-phenylimino)-imidazolidin, dessen saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben. |
-
1977
- 1977-10-18 NL NL7711390A patent/NL7711390A/xx not_active Application Discontinuation
-
1978
- 1978-09-18 ZA ZA785278A patent/ZA785278B/xx unknown
- 1978-09-27 AR AR273866A patent/AR225601A1/es active
- 1978-10-13 HU HU78PI643A patent/HU178690B/hu unknown
- 1978-10-13 CA CA313,362A patent/CA1106845A/en not_active Expired
- 1978-10-13 IL IL55728A patent/IL55728A/xx unknown
- 1978-10-13 DK DK458178A patent/DK458178A/da not_active Application Discontinuation
- 1978-10-13 IT IT28761/78A patent/IT1099744B/it active
- 1978-10-16 ES ES474227A patent/ES474227A1/es not_active Expired
- 1978-10-16 JP JP12724678A patent/JPS5463080A/ja active Granted
- 1978-10-16 TR TR20567A patent/TR20567A/xx unknown
- 1978-10-16 DE DE7878200241T patent/DE2861822D1/de not_active Expired
- 1978-10-16 NZ NZ188660A patent/NZ188660A/xx unknown
- 1978-10-16 AU AU40754/78A patent/AU521181B2/en not_active Expired
- 1978-10-16 CS CS786730A patent/CS208757B2/cs unknown
- 1978-10-16 CS CS786730A patent/CS208758B2/cs unknown
- 1978-10-16 PL PL1978210324A patent/PL120588B1/pl unknown
- 1978-10-16 DD DD78208481A patent/DD139989A5/de unknown
- 1978-10-16 PL PL21699678A patent/PL216996A1/xx unknown
- 1978-10-16 EP EP78200241A patent/EP0001663B1/en not_active Expired
- 1978-10-16 DD DD78217704A patent/DD147846A5/de unknown
- 1978-10-17 EG EG606/78A patent/EG13497A/xx active
-
1979
- 1979-03-21 SU SU792739504A patent/SU895289A3/ru active
- 1979-05-02 ES ES480166A patent/ES480166A1/es not_active Expired
-
1980
- 1980-02-28 SU SU802891001A patent/SU969160A3/ru active
-
1981
- 1981-05-18 US US06/264,461 patent/US4396617A/en not_active Expired - Fee Related
- 1981-05-18 US US06/264,460 patent/US4374143A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IT7828761A0 (it) | 1978-10-13 |
| EP0001663A1 (en) | 1979-05-02 |
| ES480166A1 (es) | 1979-12-16 |
| HU178690B (en) | 1982-06-28 |
| AU4075478A (en) | 1980-04-24 |
| NL7711390A (nl) | 1979-04-20 |
| SU895289A3 (ru) | 1981-12-30 |
| IT1099744B (it) | 1985-09-28 |
| TR20567A (tr) | 1982-01-01 |
| SU969160A3 (ru) | 1982-10-23 |
| JPS5463080A (en) | 1979-05-21 |
| NZ188660A (en) | 1980-03-05 |
| US4396617A (en) | 1983-08-02 |
| PL210324A1 (ko) | 1980-03-10 |
| CS208758B2 (en) | 1981-09-15 |
| DD139989A5 (de) | 1980-02-06 |
| CS208757B2 (en) | 1981-09-15 |
| ZA785278B (en) | 1980-05-28 |
| DK458178A (da) | 1979-04-19 |
| AU521181B2 (en) | 1982-03-18 |
| ES474227A1 (es) | 1979-10-16 |
| CA1106845A (en) | 1981-08-11 |
| US4374143A (en) | 1983-02-15 |
| PL120588B1 (en) | 1982-03-31 |
| AR225601A1 (es) | 1982-04-15 |
| DE2861822D1 (en) | 1982-07-01 |
| PL216996A1 (ko) | 1980-07-14 |
| IL55728A0 (en) | 1978-12-17 |
| EP0001663B1 (en) | 1982-05-12 |
| EG13497A (en) | 1982-06-30 |
| IL55728A (en) | 1982-05-31 |
| JPS6141353B2 (ko) | 1986-09-13 |
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