SU1061697A3 - Способ получени замещенных тетрагидропиримидинов - Google Patents

Способ получени замещенных тетрагидропиримидинов Download PDF

Info

Publication number: SU1061697A3
Authority: SU; USSR - Soviet Union
Prior art keywords: methyl; dione; tetrahydropyranyl; alkyl; ethyl
Prior art date: 1970-03-26

Application number

SU711626609A

Other languages

English (en)

Russian (ru)

Inventor

Бертэн Даниель

Перронэ Жак

Теш Андрэ

Original Assignee

Руссель-Уклаф (Фирма)

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.)

1970-03-26

Filing date

1971-03-16

Publication date

1983-12-15

1970-03-26 Priority claimed from FR7010906A external-priority patent/FR2082768A5/fr

1971-03-16 Application filed by Руссель-Уклаф (Фирма) filed Critical Руссель-Уклаф (Фирма)

1983-12-15 Application granted granted Critical

1983-12-15 Publication of SU1061697A3 publication Critical patent/SU1061697A3/ru

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
150000005326 tetrahydropyrimidines Chemical class 0.000 title claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
-1 tetrahydrofuranyl isocyanic acid ester Chemical class 0.000 claims description 39
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 37
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
238000009835 boiling Methods 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
229920000742 Cotton Polymers 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 24
238000010992 reflux Methods 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000002244 precipitate Substances 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
235000019441 ethanol Nutrition 0.000 description 16
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
239000000047 product Substances 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000002253 acid Substances 0.000 description 6
230000018044 dehydration Effects 0.000 description 6
238000006297 dehydration reaction Methods 0.000 description 6
238000004821 distillation Methods 0.000 description 6
239000012071 phase Substances 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
125000004494 ethyl ester group Chemical group 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
DRAABUZZLREBAU-UHFFFAOYSA-N 2-isocyanatooxolane Chemical compound O=C=NC1CCCO1 DRAABUZZLREBAU-UHFFFAOYSA-N 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
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 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000002363 herbicidal effect Effects 0.000 description 4
150000003949 imides Chemical group 0.000 description 4
239000010410 layer Substances 0.000 description 4
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
VXVWIRKAABQIGS-UHFFFAOYSA-N 2-isocyanatooxane Chemical compound O=C=NC1CCCCO1 VXVWIRKAABQIGS-UHFFFAOYSA-N 0.000 description 3
VERRCQLXPASQDJ-UHFFFAOYSA-N 5,6-dimethyl-3-(oxan-2-yl)-1h-pyrimidine-2,4-dione Chemical compound O=C1C(C)=C(C)NC(=O)N1C1OCCCC1 VERRCQLXPASQDJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000003306 harvesting Methods 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
DJXCMMGXAQUXKT-UHFFFAOYSA-N 3-(oxan-2-yl)-6-propyl-1H-pyrimidine-2,4-dione Chemical compound O1C(CCCC1)N1C(NC(=CC1=O)CCC)=O DJXCMMGXAQUXKT-UHFFFAOYSA-N 0.000 description 2
FNAXWZQFXYCTQZ-UHFFFAOYSA-N 5,6-diethyl-3-(oxan-2-yl)-1h-pyrimidine-2,4-dione Chemical compound O=C1C(CC)=C(CC)NC(=O)N1C1OCCCC1 FNAXWZQFXYCTQZ-UHFFFAOYSA-N 0.000 description 2
BKSKZOLOACHQJX-UHFFFAOYSA-N 5-chloro-3-(oxan-2-yl)-6-propyl-1H-pyrimidine-2,4-dione Chemical compound O1C(CCCC1)N1C(NC(=C(C1=O)Cl)CCC)=O BKSKZOLOACHQJX-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000743339 Agrostis Species 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
241000219793 Trifolium Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000000034 method Methods 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
ZNYNWQOXYGEQIF-WAYWQWQTSA-N (Z)-3-amino-2-methylhex-2-enoic acid Chemical compound CCC\C(N)=C(/C)C(O)=O ZNYNWQOXYGEQIF-WAYWQWQTSA-N 0.000 description 1
UYPQCGHDGAGZHI-PLNGDYQASA-N (z)-3-amino-2-ethylbut-2-enoic acid Chemical compound CC\C(=C(/C)N)C(O)=O UYPQCGHDGAGZHI-PLNGDYQASA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
ZVAKZVDJIUFFFP-UHFFFAOYSA-N 2-chlorooxolane Chemical compound ClC1CCCO1 ZVAKZVDJIUFFFP-UHFFFAOYSA-N 0.000 description 1
COJKZHVHZYKHER-UHFFFAOYSA-N 2-propanoylhexanoic acid Chemical compound CCCCC(C(O)=O)C(=O)CC COJKZHVHZYKHER-UHFFFAOYSA-N 0.000 description 1
YTLYLLTVENPWFT-UHFFFAOYSA-N 3-aminoprop-2-enoic acid Chemical compound NC=CC(O)=O YTLYLLTVENPWFT-UHFFFAOYSA-N 0.000 description 1
CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
GUDISQVTDMSLGN-UHFFFAOYSA-N 5-bromo-6-methyl-3-(oxan-2-yl)-1H-pyrimidine-2,4-dione Chemical compound O1C(CCCC1)N1C(NC(=C(C1=O)Br)C)=O GUDISQVTDMSLGN-UHFFFAOYSA-N 0.000 description 1
YFTMPDGCVOWZOZ-UHFFFAOYSA-N 5-chloro-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)NC(=O)C=1Cl YFTMPDGCVOWZOZ-UHFFFAOYSA-N 0.000 description 1
UWOPKGUIQOULAE-UHFFFAOYSA-N 5-chloro-6-methyl-3-(oxan-2-yl)-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Cl)=C(C)NC(=O)N1C1OCCCC1 UWOPKGUIQOULAE-UHFFFAOYSA-N 0.000 description 1
KSFTTXBCYNRMGU-UHFFFAOYSA-N 6-methyl-3-(oxan-2-yl)-5-propan-2-yl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(C(C)C)=C(C)NC(=O)N1C1OCCCC1 KSFTTXBCYNRMGU-UHFFFAOYSA-N 0.000 description 1
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
240000001592 Amaranthus caudatus Species 0.000 description 1
235000009328 Amaranthus caudatus Nutrition 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
244000144730 Amygdalus persica Species 0.000 description 1
235000021537 Beetroot Nutrition 0.000 description 1
244000056139 Brassica cretica Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000007516 Chrysanthemum Nutrition 0.000 description 1
244000189548 Chrysanthemum x morifolium Species 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
240000005702 Galium aparine Species 0.000 description 1
235000014820 Galium aparine Nutrition 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
240000004296 Lolium perenne Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
235000006040 Prunus persica var persica Nutrition 0.000 description 1
241000219053 Rumex Species 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
CAMXVZOXBADHNJ-UHFFFAOYSA-N ammonium nitrite Chemical compound [NH4+].[O-]N=O CAMXVZOXBADHNJ-UHFFFAOYSA-N 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 1
BUBWTSJXUHKBBX-UHFFFAOYSA-N ethyl acetate;sodium Chemical compound [Na].CCOC(C)=O BUBWTSJXUHKBBX-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
238000005360 mashing Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
244000045947 parasite Species 0.000 description 1
239000003415 peat Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000004576 sand Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000000126 substance Substances 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
JDSSVQWHYUVDDF-UPHRSURJSA-N ureidoacrylic acid Chemical compound NC(=O)N\C=C/C(O)=O JDSSVQWHYUVDDF-UPHRSURJSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009333 weeding Methods 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

SU711626609A 1970-03-26 1971-03-16 Способ получени замещенных тетрагидропиримидинов SU1061697A3 (ru)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
FR7010906A FR2082768A5 (2)	1970-03-26	1970-03-26
FR7102829A FR2123184B2 (2)	1970-03-26	1971-01-28
FR7106436A FR2127143A5 (2)	1970-03-26	1971-02-25

Publications (1)

Publication Number	Publication Date
SU1061697A3 true SU1061697A3 (ru)	1983-12-15

Family

ID=27249315

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU711626609A SU1061697A3 (ru)	1970-03-26	1971-03-16	Способ получени замещенных тетрагидропиримидинов

Country Status (3)

Country	Link
JP (1)	JPS5414108B1 (2)
IL (1)	IL36392A (2)
SU (1)	SU1061697A3 (2)

1971
- 1971-03-11 IL IL36392A patent/IL36392A/xx unknown
- 1971-03-16 SU SU711626609A patent/SU1061697A3/ru active
- 1971-03-26 JP JP1732371A patent/JPS5414108B1/ja active Pending

Also Published As

Publication number	Publication date
IL36392A (en)	1974-03-14
JPS5414108B1 (2)	1979-06-05
IL36392A0 (en)	1971-05-26

Publication	Publication Date	Title
RU2014327C1 (ru)	1994-06-15	Способ получения производных 2-анилинопиримидина
RU2037488C1 (ru)	1995-06-19	Производные 3-циано-5-алкокси-1-арилпиразолов и композиция на их основе
DE2513732C2 (2)	1988-04-14
SU1665875A3 (ru)	1991-07-23	Способ получени Е-изомеров производных акриловой кислоты
JP2017525703A (ja)	2017-09-07	３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの調製方法
SU1678212A3 (ru)	1991-09-15	Способ получени тиазолотриазоловых сульфонамидов
CN113527221B (zh)	2023-06-23	地克珠利衍生物及其应用和一种用于抗植物真菌病的杀菌剂
SU1061697A3 (ru)	1983-12-15	Способ получени замещенных тетрагидропиримидинов
SU902665A3 (ru)	1982-01-30	Способ получени тиазолилиденоксопропионитрилов
WO1996025404A1 (en)	1996-08-22	Triazine derivatives
CN109956904B (zh)	2022-03-01	吡唑酰胺类化合物及其应用和杀菌剂
IL24814A (en)	1971-04-28	N',n'-disubstituted-thiono carbamyl thiolo-imides and process for their preparation
CN105994314A (zh)	2016-10-12	骆驼宁碱a在防治蚜虫中的应用
KR840000846B1 (ko)	1984-06-19	N-(1'-하이드로카르보닐옥시카르보닐에틸)-n-알콕시 아세틸 아닐린유도체의 제조방법
US4035387A (en)	1977-07-12	1,3-Dithiol-2-ylidene malonic esters
DE2239892A1 (de)	1973-03-01	Mittel zur bekaempfung von pflanzenpathogenen organismen
JPH045276A (ja)	1992-01-09	シクロヘキサン誘導体又はその塩類及びその用途
US3811863A (en)	1974-05-21	Novel tetrahydropyrimidines
JP3054977B2 (ja)	2000-06-19	殺菌性フラノン誘導体
US4175186A (en)	1979-11-20	Biocidally-active, 1,3-benzodithiole-2-one and 1,3-benzodithiole-2-thione compounds
RU2831129C1 (ru)	2024-12-02	4-оксо-2-{ [4-фенил-3-(этоксикарбонил)тиофен-2-ил]амино)} -4-(4-фторфенил)бут-2-еновая кислота, обладающая противовоспалительной активностью
CN110590725A (zh)	2019-12-20	一类东莨菪素磺酸酯化合物及其制备与杀螨用途
RU2014326C1 (ru)	1994-06-15	Производные имидазола
WO2019154171A1 (zh)	2019-08-15	一种无污染环保型高产率制备吡虫啉的方法
KR800000430B1 (ko)	1980-05-26	α-벤질리덴 락톤 유도체류의 제조방법