CH618422A5 - Process for the preparation of sulphonylureas - Google Patents
Process for the preparation of sulphonylureas Download PDFInfo
- Publication number
- CH618422A5 CH618422A5 CH38876A CH38876A CH618422A5 CH 618422 A5 CH618422 A5 CH 618422A5 CH 38876 A CH38876 A CH 38876A CH 38876 A CH38876 A CH 38876A CH 618422 A5 CH618422 A5 CH 618422A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- bis
- reaction
- dicarboxylic acid
- dichloramide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 87
- 229940100389 Sulfonylurea Drugs 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- -1 Acid amide halides Chemical class 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 229940124530 sulfonamide Drugs 0.000 claims description 24
- 150000003456 sulfonamides Chemical class 0.000 claims description 18
- 239000011734 sodium Substances 0.000 claims description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000000732 arylene group Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 3
- UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 claims description 2
- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 claims description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 3
- 235000013877 carbamide Nutrition 0.000 claims 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- XAORHBINKHJHCC-UHFFFAOYSA-N O-ethyl N-sulfonylcarbamothioate Chemical class S(=O)(=O)=NC(=S)OCC XAORHBINKHJHCC-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000006477 desulfuration reaction Methods 0.000 claims 1
- 230000023556 desulfurization Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical class N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 claims 1
- 238000012552 review Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 150000003673 urethanes Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000725 suspension Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- SJPGVGGOTJCYTC-UHFFFAOYSA-N 1-[4-[carbamoyl-(4-methylphenyl)sulfonylamino]phenyl]-1-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C(N)=O)C1=CC=C(N(C(N)=O)S(=O)(=O)C=2C=CC(C)=CC=2)C=C1 SJPGVGGOTJCYTC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- GVOBBMKHUZFSHB-UHFFFAOYSA-N 2,4,5-trichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl GVOBBMKHUZFSHB-UHFFFAOYSA-N 0.000 description 2
- KQZFABSTXSNEQH-UHFFFAOYSA-N 4-iodobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(I)C=C1 KQZFABSTXSNEQH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 150000007945 N-acyl ureas Chemical class 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 2
- RLFFWWKJSJOYMQ-UHFFFAOYSA-N 1,3-diazepan-2-one Chemical compound O=C1NCCCCN1 RLFFWWKJSJOYMQ-UHFFFAOYSA-N 0.000 description 1
- OLSJVTLNNWLLIL-UHFFFAOYSA-N 1,3-disulfonylurea Chemical compound O=S(=O)=NC(=O)N=S(=O)=O OLSJVTLNNWLLIL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- STYQHICBPYRHQK-UHFFFAOYSA-N 4-bromobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Br)C=C1 STYQHICBPYRHQK-UHFFFAOYSA-N 0.000 description 1
- HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 description 1
- LFLSATHZMYYIAQ-UHFFFAOYSA-N 4-flourobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(F)C=C1 LFLSATHZMYYIAQ-UHFFFAOYSA-N 0.000 description 1
- 238000007167 Hofmann rearrangement reaction Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- ZRVCTYCTIIJARH-UHFFFAOYSA-N n-sulfonylcarbamoyl chloride Chemical compound ClC(=O)N=S(=O)=O ZRVCTYCTIIJARH-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- SWBLLSQMOMPTMC-UHFFFAOYSA-N naphthalene-2-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)N)=CC=C21 SWBLLSQMOMPTMC-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000010626 work up procedure 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
- C07C311/57—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
- C07C311/60—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 carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752502428 DE2502428C2 (de) | 1975-01-22 | 1975-01-22 | Verfahren zur herstellung von na- oder k-salzen von arylen- bis -sulfonylharnstoffen oder der entsprechenden arylenbis-sulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618422A5 true CH618422A5 (en) | 1980-07-31 |
Family
ID=5936990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH38876A CH618422A5 (en) | 1975-01-22 | 1976-01-15 | Process for the preparation of sulphonylureas |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5929585B2 (cg-RX-API-DMAC10.html) |
| AT (1) | AT345850B (cg-RX-API-DMAC10.html) |
| BE (1) | BE837753A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1051026A (cg-RX-API-DMAC10.html) |
| CH (1) | CH618422A5 (cg-RX-API-DMAC10.html) |
| DD (1) | DD123324A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2502428C2 (cg-RX-API-DMAC10.html) |
| ES (1) | ES444512A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2298537A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1515991A (cg-RX-API-DMAC10.html) |
| IT (1) | IT1053316B (cg-RX-API-DMAC10.html) |
| NL (1) | NL7600649A (cg-RX-API-DMAC10.html) |
| SU (1) | SU719496A3 (cg-RX-API-DMAC10.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2710595C3 (de) | 1977-03-11 | 1980-11-06 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung der Trans-Isomeren von Cyclohexan-l,4-diamin-, diurethanen, -diharnstoffen, -disulfonylharnstoffen und -diisocyanat |
| DE3019491C2 (de) * | 1980-05-22 | 1985-02-21 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von Oximcarbamaten |
| JP2789942B2 (ja) * | 1992-07-06 | 1998-08-27 | 王子製紙株式会社 | ビス（ｐ−トルエンスルホニルアミノカルボニルアミノ）ジフェニル化合物類 |
| CN111285787B (zh) * | 2020-03-09 | 2021-02-09 | 潍坊大有生物化工有限公司 | 一种新型非酚热敏显色剂、制备方法及其在热敏记录材料中的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR993465A (fr) * | 1949-06-28 | 1951-10-31 | Procédé pour la production de sulfo-dérivés de l'urée ou de la thio-urée | |
| NL218580A (cg-RX-API-DMAC10.html) * | 1960-04-28 | |||
| FR1355961A (fr) * | 1963-04-22 | 1964-03-20 | Hoechst Ag | Hydroxy-benzène-sulfonyl-urées et leur préparation |
-
1975
- 1975-01-22 DE DE19752502428 patent/DE2502428C2/de not_active Expired
-
1976
- 1976-01-06 FR FR7600164A patent/FR2298537A1/fr active Granted
- 1976-01-15 IT IT4764976A patent/IT1053316B/it active
- 1976-01-15 CH CH38876A patent/CH618422A5/de not_active IP Right Cessation
- 1976-01-16 GB GB1706/76A patent/GB1515991A/en not_active Expired
- 1976-01-16 AT AT28176A patent/AT345850B/de not_active IP Right Cessation
- 1976-01-20 DD DD19088776A patent/DD123324A5/xx unknown
- 1976-01-21 SU SU762314903A patent/SU719496A3/ru active
- 1976-01-21 BE BE163662A patent/BE837753A/xx not_active IP Right Cessation
- 1976-01-21 ES ES444512A patent/ES444512A1/es not_active Expired
- 1976-01-21 CA CA243,973A patent/CA1051026A/en not_active Expired
- 1976-01-22 JP JP633876A patent/JPS5929585B2/ja not_active Expired
- 1976-01-22 NL NL7600649A patent/NL7600649A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2502428B1 (de) | 1976-04-08 |
| AT345850B (de) | 1978-10-10 |
| SU719496A3 (ru) | 1980-02-29 |
| DD123324A5 (cg-RX-API-DMAC10.html) | 1976-12-12 |
| FR2298537A1 (fr) | 1976-08-20 |
| NL7600649A (nl) | 1976-07-26 |
| BE837753A (fr) | 1976-05-14 |
| GB1515991A (en) | 1978-06-28 |
| CA1051026A (en) | 1979-03-20 |
| ATA28176A (de) | 1978-02-15 |
| DE2502428C2 (de) | 1976-11-18 |
| IT1053316B (it) | 1981-08-31 |
| FR2298537B1 (cg-RX-API-DMAC10.html) | 1980-07-25 |
| JPS5198241A (en) | 1976-08-30 |
| JPS5929585B2 (ja) | 1984-07-21 |
| ES444512A1 (es) | 1977-05-16 |
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