JPS5831341B2 - 尿素誘導体、置換アシル尿素およびスルホニル尿素誘導体の製造法 - Google Patents
尿素誘導体、置換アシル尿素およびスルホニル尿素誘導体の製造法Info
- Publication number
- JPS5831341B2 JPS5831341B2 JP49131845A JP13184574A JPS5831341B2 JP S5831341 B2 JPS5831341 B2 JP S5831341B2 JP 49131845 A JP49131845 A JP 49131845A JP 13184574 A JP13184574 A JP 13184574A JP S5831341 B2 JPS5831341 B2 JP S5831341B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- cyanamide
- groups
- substituted
- 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
- 150000003672 ureas Chemical class 0.000 title description 7
- 150000007945 N-acyl ureas Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 19
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
- 239000011968 lewis acid catalyst Substances 0.000 claims 1
- -1 carbonium ion Chemical class 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 15
- 235000013877 carbamide Nutrition 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 239000003708 ampul Substances 0.000 description 8
- 150000001912 cyanamides Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RHENFPGQOKCWDK-UHFFFAOYSA-N (2,3-dimethylphenyl)cyanamide Chemical compound CC1=CC=CC(NC#N)=C1C RHENFPGQOKCWDK-UHFFFAOYSA-N 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 229940100389 Sulfonylurea Drugs 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006434 Ritter amidation reaction Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 2
- GKFFFNUVYUGXEW-UHFFFAOYSA-N (4-chlorophenyl)cyanamide Chemical compound ClC1=CC=C(NC#N)C=C1 GKFFFNUVYUGXEW-UHFFFAOYSA-N 0.000 description 2
- FCLSEQZSHNXQBR-UHFFFAOYSA-N (4-methylphenyl)cyanamide Chemical compound CC1=CC=C(NC#N)C=C1 FCLSEQZSHNXQBR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- VRBVHQUSAOKVDH-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1 VRBVHQUSAOKVDH-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- NCNOXAARNNOPJA-UHFFFAOYSA-N N#CNC(C(C(C=CC=C1)=C1Cl)OC(C=CC(Cl)=C1)=C1Cl)=O Chemical compound N#CNC(C(C(C=CC=C1)=C1Cl)OC(C=CC(Cl)=C1)=C1Cl)=O NCNOXAARNNOPJA-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- PWZKESLISFPGHR-UHFFFAOYSA-N (2-chlorophenyl)cyanamide Chemical compound ClC1=CC=CC=C1NC#N PWZKESLISFPGHR-UHFFFAOYSA-N 0.000 description 1
- VGQKZVPHFLOGTN-UHFFFAOYSA-N (3,4-dichlorophenyl)cyanamide Chemical compound ClC1=CC=C(NC#N)C=C1Cl VGQKZVPHFLOGTN-UHFFFAOYSA-N 0.000 description 1
- ZFQMSPFLYBUSLE-UHFFFAOYSA-N (3,5-dimethylphenyl)cyanamide Chemical compound CC1=CC(C)=CC(NC#N)=C1 ZFQMSPFLYBUSLE-UHFFFAOYSA-N 0.000 description 1
- DCMFSSNEAKEHAM-UHFFFAOYSA-N (3-chlorophenyl)cyanamide Chemical compound ClC1=CC=CC(NC#N)=C1 DCMFSSNEAKEHAM-UHFFFAOYSA-N 0.000 description 1
- HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- ABYSGRXBGLVRGO-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetyl chloride Chemical compound CC1=CC(Cl)=CC=C1OCC(Cl)=O ABYSGRXBGLVRGO-UHFFFAOYSA-N 0.000 description 1
- TWFQQPGUKKGVRY-UHFFFAOYSA-N 2-chloro-n-cyanoacetamide Chemical compound ClCC(=O)NC#N TWFQQPGUKKGVRY-UHFFFAOYSA-N 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 1
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- PMEMEAJBKORTFG-UHFFFAOYSA-N CC(C=C1)=CC=C1C1=CC=CC(S(NC#N)(=O)=O)=C1[N+]([O-])=O Chemical compound CC(C=C1)=CC=C1C1=CC=CC(S(NC#N)(=O)=O)=C1[N+]([O-])=O PMEMEAJBKORTFG-UHFFFAOYSA-N 0.000 description 1
- XJIQGUQHEOGADJ-UHFFFAOYSA-N CC1=CC=CC(C(C(NC#N)=O)OC(C=C2)=C(C)C=C2Cl)=C1C Chemical compound CC1=CC=CC(C(C(NC#N)=O)OC(C=C2)=C(C)C=C2Cl)=C1C XJIQGUQHEOGADJ-UHFFFAOYSA-N 0.000 description 1
- CEVHMAKWLSMGPM-UHFFFAOYSA-N CC1=CC=CC(N(C(N)=O)S(C)(=O)=O)=C1C Chemical compound CC1=CC=CC(N(C(N)=O)S(C)(=O)=O)=C1C CEVHMAKWLSMGPM-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- QPTBGLCRVLBHBC-UHFFFAOYSA-N N#CNC(C(C(C=C1)=CC(Cl)=C1Cl)OC(C=CC(Cl)=C1)=C1Cl)=O Chemical compound N#CNC(C(C(C=C1)=CC(Cl)=C1Cl)OC(C=CC(Cl)=C1)=C1Cl)=O QPTBGLCRVLBHBC-UHFFFAOYSA-N 0.000 description 1
- YYZDFIRKBPDFLA-UHFFFAOYSA-N N#CNC(C(C(C=C1)=CC=C1Cl)OC(C=CC(Cl)=C1)=C1Cl)=O Chemical compound N#CNC(C(C(C=C1)=CC=C1Cl)OC(C=CC(Cl)=C1)=C1Cl)=O YYZDFIRKBPDFLA-UHFFFAOYSA-N 0.000 description 1
- KJGFYKUVFNVMQJ-UHFFFAOYSA-N N#CNC(C(C(C=CC=C1)=C1Cl)OC(C=C1)=CC=C1Cl)=O Chemical compound N#CNC(C(C(C=CC=C1)=C1Cl)OC(C=C1)=CC=C1Cl)=O KJGFYKUVFNVMQJ-UHFFFAOYSA-N 0.000 description 1
- ZFBVARRVRNCGJP-UHFFFAOYSA-N N#CNC(C(C1=CC(Cl)=CC=C1)OC(C=C1)=CC=C1Cl)=O Chemical compound N#CNC(C(C1=CC(Cl)=CC=C1)OC(C=C1)=CC=C1Cl)=O ZFBVARRVRNCGJP-UHFFFAOYSA-N 0.000 description 1
- WBNBVZHEQMLYAH-UHFFFAOYSA-N N-(tert-butylcarbamoyl)-N-(4-methylphenyl)benzamide Chemical compound CC1=CC=C(C=C1)N(C(=O)NC(C)(C)C)C(C1=CC=CC=C1)=O WBNBVZHEQMLYAH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical group CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical compound CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002542 isoureas Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PTECIXPBVVDNOU-UHFFFAOYSA-N molecular bromine;hydrate Chemical compound O.BrBr PTECIXPBVVDNOU-UHFFFAOYSA-N 0.000 description 1
- RNIOTFCFTCRCFM-UHFFFAOYSA-N n-cyano-3,4,5-trimethoxybenzamide Chemical compound COC1=CC(C(=O)NC#N)=CC(OC)=C1OC RNIOTFCFTCRCFM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- IBQCYUBVFOFMRI-UHFFFAOYSA-N tert-butylcyanamide Chemical compound CC(C)(C)NC#N IBQCYUBVFOFMRI-UHFFFAOYSA-N 0.000 description 1
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/55—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/58—Y being a hetero atom
- C07C275/60—Y being an oxygen atom, e.g. allophanic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7340527A FR2271202A1 (en) | 1973-11-14 | 1973-11-14 | Substituted ureas, acylureas and sulphonylureas prodn - by reacting a substituted cyanamide with a cpd forming a carbonium ion |
| FR7435907A FR2288735A2 (fr) | 1974-10-25 | 1974-10-25 | Derives de l'uree, acylurees et sulfonylurees substituees et leur procede de fabrication |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5083331A JPS5083331A (enExample) | 1975-07-05 |
| JPS5831341B2 true JPS5831341B2 (ja) | 1983-07-05 |
Family
ID=26218025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49131845A Expired JPS5831341B2 (ja) | 1973-11-14 | 1974-11-14 | 尿素誘導体、置換アシル尿素およびスルホニル尿素誘導体の製造法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4013706A (enExample) |
| JP (1) | JPS5831341B2 (enExample) |
| CH (1) | CH605700A5 (enExample) |
| DE (2) | DE2454107B2 (enExample) |
| GB (2) | GB1476797A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6033109B2 (ja) * | 1977-04-28 | 1985-08-01 | 塩野義製薬株式会社 | 尿素誘導体の合成法 |
| DE2733181B2 (de) * | 1977-07-22 | 1979-08-30 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von N-substituierten a -Ketocarbonsäureamiden |
| DE2919292A1 (de) * | 1979-05-12 | 1980-11-20 | Bayer Ag | Substituierte harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als pflanzenbakterizide |
| DE2934248A1 (de) | 1979-08-24 | 1981-03-26 | Hoechst Ag, 65929 Frankfurt | Wasserloesliche phthalocyaninverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| DE2934247A1 (de) * | 1979-08-24 | 1981-04-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur veredlung von faserigen materialien |
| US4399152A (en) * | 1980-04-03 | 1983-08-16 | Duphar International B.V. | Substituted benzoyl ureas as insecticides |
| DE3035393A1 (de) * | 1980-09-19 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung vonn-substituierten imidodicarbonsaeurediarylestern |
| US4618712A (en) * | 1982-02-23 | 1986-10-21 | Ciba-Geigy Corporation | N-cyanocarboxylic acid amides, processes for their preparation and their use |
| GB2226815A (en) * | 1989-01-06 | 1990-07-11 | Shell Int Research | Fungicidal n-acyl cyanamides |
| US5254589A (en) * | 1991-10-15 | 1993-10-19 | Warner-Lambert Company | Sulfonyl urea and carbamate ACAT inhibitors |
| HU228303B1 (hu) * | 1999-07-13 | 2013-03-28 | Lonza Ag | Eljárás 2-amino-4-(4-fluorfenil)-6-alkil-pirimidin-5-karboxilát-származékok elõállítására |
| CN106008260A (zh) * | 2016-06-08 | 2016-10-12 | 刘利楠 | 一种芳氰基化合物的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427323A (en) * | 1964-07-16 | 1969-02-11 | Du Pont | Alpha-alkoxyalkylcyanamides and their preparation |
| US3332994A (en) * | 1966-06-17 | 1967-07-25 | Du Pont | Alkoxycyanamides and their preparation |
| NL160809C (nl) * | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
-
1974
- 1974-11-13 US US05/523,550 patent/US4013706A/en not_active Expired - Lifetime
- 1974-11-14 DE DE19742454107 patent/DE2454107B2/de active Granted
- 1974-11-14 GB GB4967875A patent/GB1476797A/en not_active Expired
- 1974-11-14 CH CH1520374A patent/CH605700A5/xx not_active IP Right Cessation
- 1974-11-14 JP JP49131845A patent/JPS5831341B2/ja not_active Expired
- 1974-11-14 DE DE2462011A patent/DE2462011C3/de not_active Expired
- 1974-11-14 GB GB4931974A patent/GB1476796A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2454107A1 (de) | 1975-05-22 |
| CH605700A5 (enExample) | 1978-10-13 |
| JPS5083331A (enExample) | 1975-07-05 |
| DE2462011C3 (de) | 1978-05-03 |
| US4013706A (en) | 1977-03-22 |
| DE2462011A1 (de) | 1975-06-26 |
| DE2462011B2 (de) | 1977-09-22 |
| DE2454107B2 (de) | 1977-01-13 |
| GB1476797A (en) | 1977-06-16 |
| GB1476796A (en) | 1977-06-16 |
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