NL8900534A - Werkwijze voor de bereiding van n-sulfonylureumderivaten. - Google Patents

Werkwijze voor de bereiding van n-sulfonylureumderivaten. Download PDF

Info

Publication number: NL8900534A
Authority: NL; Netherlands
Prior art keywords: general formula; catalyst; process according; halo; halogen
Prior art date: 1988-03-04

Application number

NL8900534A

Other languages

English (en)

Dutch (nl)

Original Assignee

Nitrokemia Ipartelepek

Priority date (The priority date 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 date listed.)

1988-03-04

Filing date

1989-03-03

Publication date

1989-10-02

1989-03-03 Application filed by Nitrokemia Ipartelepek filed Critical Nitrokemia Ipartelepek

1989-10-02 Publication of NL8900534A publication Critical patent/NL8900534A/nl

Links

238000000034 method Methods 0.000 title claims description 34
230000008569 process Effects 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 9
239000003054 catalyst Substances 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 24
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 19
229910002091 carbon monoxide Inorganic materials 0.000 claims description 19
239000011541 reaction mixture Substances 0.000 claims description 15
-1 N-chloramino Chemical group 0.000 claims description 14
238000003763 carbonization Methods 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
239000003444 phase transfer catalyst Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
150000004982 aromatic amines Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
USHHCQFIUMQAKY-UHFFFAOYSA-N 4-methoxy-6-methyl-1h-triazin-2-amine Chemical compound COC1=NN(N)NC(C)=C1 USHHCQFIUMQAKY-UHFFFAOYSA-N 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
125000004421 aryl sulphonamide group Chemical group 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 5
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 claims description 5
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000011591 potassium Chemical group 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
229910001414 potassium ion Inorganic materials 0.000 claims description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
238000005255 carburizing Methods 0.000 claims description 3
150000003983 crown ethers Chemical group 0.000 claims description 3
239000002815 homogeneous catalyst Substances 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
150000004714 phosphonium salts Chemical group 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000012298 atmosphere Substances 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
239000000700 radioactive tracer Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
229910001415 sodium ion Inorganic materials 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000004306 triazinyl group Chemical group 0.000 claims description 2
150000002739 metals Chemical class 0.000 claims 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 7
229910002666 PdCl2 Inorganic materials 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229940124530 sulfonamide Drugs 0.000 description 4
150000003456 sulfonamides Chemical class 0.000 description 4
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229940100389 Sulfonylurea Drugs 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000005005 aminopyrimidines Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
QZJFMJCWOPZNJY-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=CC=C1Cl QZJFMJCWOPZNJY-UHFFFAOYSA-N 0.000 description 2
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000003426 co-catalyst Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical group 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
NAGPHJSLVDZREE-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-(4-methoxy-6-methyltriazin-5-yl)urea Chemical compound COC1=NN=NC(C)=C1NC(=O)NS(=O)(=O)C1=CC=CC=C1Br NAGPHJSLVDZREE-UHFFFAOYSA-N 0.000 description 1
VSOOBQALJVLTBH-UHFFFAOYSA-N 2-aminosulfonyl-benzoic acid methyl ester Chemical compound COC(=O)C1=CC=CC=C1S(N)(=O)=O VSOOBQALJVLTBH-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
OESNKOYDYYELPO-UHFFFAOYSA-N ClNN1NC(=CC(=N1)C)OC Chemical compound ClNN1NC(=CC(=N1)C)OC OESNKOYDYYELPO-UHFFFAOYSA-N 0.000 description 1
102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
IHKDOTNWRDNHGG-UHFFFAOYSA-N N1C(OC)=CC(C)=NN1NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 Chemical compound N1C(OC)=CC(C)=NN1NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 IHKDOTNWRDNHGG-UHFFFAOYSA-N 0.000 description 1
229910019093 NaOCl Inorganic materials 0.000 description 1
101150003085 Pdcl gene Proteins 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000158147 Sator Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229940059260 amidate Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
244000309464 bull Species 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
238000010000 carbonizing Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010265 fast atom bombardment Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
239000003622 immobilized catalyst Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
CHVZPRDGLWBEMJ-UHFFFAOYSA-N n-chlorobenzenesulfonamide Chemical compound ClNS(=O)(=O)C1=CC=CC=C1 CHVZPRDGLWBEMJ-UHFFFAOYSA-N 0.000 description 1
BUFTYJOYPAXWBW-UHFFFAOYSA-N n-chlorotriazin-4-amine Chemical compound ClNC1=CC=NN=N1 BUFTYJOYPAXWBW-UHFFFAOYSA-N 0.000 description 1
SEKOQWZPNIJUCL-UHFFFAOYSA-N n-methylsulfonylcarbamoyl chloride Chemical class CS(=O)(=O)NC(Cl)=O SEKOQWZPNIJUCL-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
VSCGRMUDBNQJNB-UHFFFAOYSA-N pyrimidin-2-ylcarbamic acid Chemical compound OC(=O)NC1=NC=CC=N1 VSCGRMUDBNQJNB-UHFFFAOYSA-N 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000013022 venting Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero 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
- C07C311/60—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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Catalysts (AREA)

NL8900534A 1988-03-04 1989-03-03 Werkwijze voor de bereiding van n-sulfonylureumderivaten. NL8900534A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU106288		1988-03-04
HU881062A HU202487B (en)	1988-03-04	1988-03-04	Process for producing n-sulfonylureas

Publications (1)

Publication Number	Publication Date
NL8900534A true NL8900534A (nl)	1989-10-02

Family

ID=10952694

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8900534A NL8900534A (nl)	1988-03-04	1989-03-03	Werkwijze voor de bereiding van n-sulfonylureumderivaten.

Country Status (21)

Country	Link
US (1)	US4954628A (de)
JP (1)	JPH023664A (de)
CN (1)	CN1038638A (de)
AT (1)	AT397249B (de)
AU (1)	AU607312B2 (de)
BR (1)	BR8901145A (de)
CH (1)	CH678323A5 (de)
DD (1)	DD279241A5 (de)
DE (1)	DE3906910A1 (de)
DK (1)	DK100289A (de)
ES (1)	ES2010631A6 (de)
FR (1)	FR2628106B1 (de)
GB (1)	GB2216519B (de)
GR (1)	GR890100141A (de)
HU (1)	HU202487B (de)
IT (1)	IT1230068B (de)
MY (1)	MY103839A (de)
NL (1)	NL8900534A (de)
PL (1)	PL152515B1 (de)
PT (1)	PT89901B (de)
ZA (1)	ZA891642B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5166162A (en) *	1990-03-02	1992-11-24	Adir Et Compagnie	Pyridylsulfonylurea and pyridylsulfonylthiourea compounds
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1988
- 1988-03-04 HU HU881062A patent/HU202487B/hu unknown
1989
- 1989-02-28 AU AU30830/89A patent/AU607312B2/en not_active Expired - Fee Related
- 1989-03-01 DK DK100289A patent/DK100289A/da unknown
- 1989-03-02 US US07/317,769 patent/US4954628A/en not_active Expired - Fee Related
- 1989-03-03 FR FR8902771A patent/FR2628106B1/fr not_active Expired - Fee Related
- 1989-03-03 DE DE3906910A patent/DE3906910A1/de not_active Withdrawn
- 1989-03-03 PL PL1989278104A patent/PL152515B1/pl unknown
- 1989-03-03 GB GB8904946A patent/GB2216519B/en not_active Expired - Lifetime
- 1989-03-03 JP JP1051808A patent/JPH023664A/ja active Pending
- 1989-03-03 GR GR890100141A patent/GR890100141A/el unknown
- 1989-03-03 ZA ZA891642A patent/ZA891642B/xx unknown
- 1989-03-03 PT PT89901A patent/PT89901B/pt not_active IP Right Cessation
- 1989-03-03 AT AT0048289A patent/AT397249B/de not_active IP Right Cessation
- 1989-03-03 NL NL8900534A patent/NL8900534A/nl not_active Application Discontinuation
- 1989-03-03 IT IT8919652A patent/IT1230068B/it active
- 1989-03-03 CH CH797/89A patent/CH678323A5/de not_active IP Right Cessation
- 1989-03-03 DD DD89326244A patent/DD279241A5/de not_active IP Right Cessation
- 1989-03-03 ES ES8901091A patent/ES2010631A6/es not_active Expired
- 1989-03-04 CN CN89102524A patent/CN1038638A/zh active Pending
- 1989-03-06 MY MYPI89000275A patent/MY103839A/en unknown
- 1989-03-06 BR BR898901145A patent/BR8901145A/pt not_active Application Discontinuation

Also Published As

Publication number	Publication date
IT8919652A0 (it)	1989-03-03
CN1038638A (zh)	1990-01-10
FR2628106B1 (fr)	1993-06-04
AU3083089A (en)	1989-09-07
PL152515B1 (en)	1991-01-31
GB2216519B (en)	1991-12-11
CH678323A5 (de)	1991-08-30
AT397249B (de)	1994-02-25
DK100289A (da)	1989-10-02
IT1230068B (it)	1991-10-05
DK100289D0 (da)	1989-03-01
GB2216519A (en)	1989-10-11
HU202487B (en)	1991-03-28
PT89901B (pt)	1994-05-31
AU607312B2 (en)	1991-02-28
GR890100141A (el)	1990-01-19
ES2010631A6 (es)	1989-11-16
BR8901145A (pt)	1989-10-31
DD279241A5 (de)	1990-05-30
PT89901A (pt)	1989-11-10
JPH023664A (ja)	1990-01-09
DE3906910A1 (de)	1989-09-21
ATA48289A (de)	1993-07-15
US4954628A (en)	1990-09-04
GB8904946D0 (en)	1989-04-12
ZA891642B (en)	1990-01-31
MY103839A (en)	1993-09-30
FR2628106A1 (fr)	1989-09-08
PL278104A1 (en)	1989-11-13

Legal Events

Date	Code	Title	Description
1989-10-02	A1B	A search report has been drawn up
1992-11-02	BV	The patent application has lapsed

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