CS276128B6 - 1-substituted 3-(2-cyanophenyl)-thioureas and method of making same - Google Patents
1-substituted 3-(2-cyanophenyl)-thioureas and method of making same Download PDFInfo
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- CS276128B6 CS276128B6 CS394588A CS394588A CS276128B6 CS 276128 B6 CS276128 B6 CS 276128B6 CS 394588 A CS394588 A CS 394588A CS 394588 A CS394588 A CS 394588A CS 276128 B6 CS276128 B6 CS 276128B6
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- dichloromethane
- cyanophenyl
- substituted
- petroleum ether
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- 238000004519 manufacturing process Methods 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 cyanobenzonitrile amines Chemical class 0.000 claims abstract description 14
- 239000003208 petroleum Substances 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims abstract description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract description 3
- GDHYPPBFBJXNRE-UHFFFAOYSA-N 2-isothiocyanatobenzonitrile Chemical compound S=C=NC1=CC=CC=C1C#N GDHYPPBFBJXNRE-UHFFFAOYSA-N 0.000 claims description 11
- 150000003585 thioureas Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000001766 physiological effect Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- JNKLQFHXYCVOQX-UHFFFAOYSA-N (2-cyanophenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1C#N JNKLQFHXYCVOQX-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- JBKOJVQVXABCOT-UHFFFAOYSA-N 1-(2-cyanophenyl)-3-cyclohexylthiourea Chemical compound C=1C=CC=C(C#N)C=1NC(=S)NC1CCCCC1 JBKOJVQVXABCOT-UHFFFAOYSA-N 0.000 description 1
- URXIJEGTYRMMJJ-UHFFFAOYSA-N 1-(2-cyanophenyl)-3-phenylthiourea Chemical compound C=1C=CC=C(C#N)C=1NC(=S)NC1=CC=CC=C1 URXIJEGTYRMMJJ-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Rašeni ae týká 1-substituovaných 3-(2- -kyanfenyljthiomočovln obecného vzorce I, kde R znamená 4-bromfenyl, 4-chlorfenyl, 4-tolyl, 4-methoxyfenyl, 4-hydroxyfenyl, cyklohexyl, iaopropyl, terč, butýl, anillnoakupinu a způsobu jejich přípravy reakci 2-isothlokyanatobenzonitrilu s primárními aminy v prostředí dlchlormethan-petrplether při teplotě 0 až 20 °C. Látky obecného vzorce I ae používají k syntéze Ν,Ν'-disubetituovaných, resp. N,N,N'-trisubstituovaných N"-(2-kyanfenyl)-guanidinů a pro přípravu 3-, resp. 4-substituovaných chinazollnů, které pro své fyziologické účinky nacházejí uplatněni ve farmacii a v zemědělství.Sprouting and refers to 1-substituted 3- (2- cyanophenylthiourea of formula I wherein R is 4-bromophenyl, 4-chlorophenyl, 4-tolyl, 4-methoxyphenyl, 4-hydroxyphenyl, cyclohexyl, iaopropyl, target, butyl, aniline and the process for preparing the reaction Primary 2-isothkylene cyanobenzonitrile amines in dichloromethane-petroleum ether at 0 to 20 ° C. General Substances formula I and e are used for synthesis Ν, Ν'-disubetitated, respectively. N, N, N'-trisubstituted N "- (2-cyanophenyl) guanidines and for the preparation of 3-, resp. 4-substituted quinazolls that for your physiological effects found in pharmacy and in agriculture.
Description
Vynález se týká l-substituovaných-3-(2-kyanfenyl)thiomočovin obecného vzorce IThe invention relates to 1-substituted-3- (2-cyanophenyl) thioureas of formula I.
kde R znamená 4-bromfenyl, 4-chlorfenyl, 4-tolyl, 4-methoxyfenyl, 4-hydroxyfenyl, cyklohexyl, isopropyl, terč, butyl, anilinoskupinu a způsob jejich přípravy reakcí 2-isothiokyanatobenzonitrilu 9 primárními aminy v prostředí dichlormethan-petrolether při teplotě 0 až 20 °C.wherein R is 4-bromophenyl, 4-chlorophenyl, 4-tolyl, 4-methoxyphenyl, 4-hydroxyphenyl, cyclohexyl, isopropyl, tert, butyl, anilino and a process for their preparation by reaction of 2-isothiocyanatobenzonitrile 9 with primary amines in dichloromethane-petroleum ether at 0 to 20 ° C.
Látky obecného vzorce I a způsob jejich přípravy nebyly doposud popsány. Z literatury je známo, že příbuznou l-fenyl-3-(2-kyanfenyl)thiomočovinu lze připravit buď reakcí fenylisothlokyanátu s anilinem bez přítomnosti rozpouštědla při teplotě 50 - 2 °C po dobu 20 hodin ve výtěžku 85 % (+) nebo reakcí 2-isothiokyanatobenzonitrilu s anilinem za laboratorní teploty ve směsi dichlormethan-petrolether (1 : 1) ve výtěžku 98 % ( *Taylor E. C., Ravindranathan R. V.. 3. Org. Chem. 27 (1962) 2622; Pazdera P., Ondráček 0., PV 1747-88; Pazdera P., Nováček E., Ondráček 0., Chem. zvěsti, v tisku).The compounds of the formula I and the process for their preparation have not yet been described. It is known from the literature that the related 1-phenyl-3- (2-cyanophenyl) thiourea can be prepared either by reacting phenyl isothloocyanate with aniline in the absence of solvent at 50-2 ° C for 20 hours in 85% (+) yield or by reaction 2 -isothiocyanatobenzonitrile with aniline at room temperature in a mixture of dichloromethane and petroleum ether (1: 1) in a yield of 98% (* Taylor EC, Ravindranathan RV. 3. Org. Chem. 27 (1962) 2622; Pazdera P., Ondráček 0., PV 1747-88; Pazdera P., Nováček E., Ondráček 0., Chemical Rumors, in press).
Nyní bylo nalezeno, že látky obecného vzorce I lze připravit reakcí 2-isothiokyanatobenzonitrilu s primárními aminy ve směsi dichlormethan-petrolether při teplotě 0 až 20 °C ve výtěžku 78 až 96 %.It has now been found that compounds of formula I can be prepared by reacting 2-isothiocyanatobenzonitrile with primary amines in dichloromethane-petroleum ether at 0-20 ° C in 78-96% yield.
Přiklad 1Example 1
K roztoku 2-isothiokyanatobenzonitrilu (8 g, 0,05 mol) ve 100 cm dichlormethan-petrolether (1 : 1) byl při teplotě 20 °C přidán roztok 4-bromanilinu (8,6 g, 0,05 mol) v 50 cm dichlormethanu. Směs byla míchána 4 hodiny při teplotě 20 °C, potom byly krystaly odsáty, promyty dichlormethanem a vysušeny ve vakuu.To a solution of 2-isothiocyanatobenzonitrile (8 g, 0.05 mol) in 100 cm of dichloromethane-petroleum ether (1: 1) at 20 ° C was added a solution of 4-bromoaniline (8.6 g, 0.05 mol) in 50 cm dichloromethane. The mixture was stirred at 20 DEG C. for 4 hours, then the crystals were filtered off with suction, washed with dichloromethane and dried in vacuo.
Bílé krystaly, teplota tání 239 až 241 °C.White crystals, m.p. 239-241 ° C.
Výtěžek l-(4-bromfenyl)-3-(kyanfenyl)thiomočoviny 15,8 g (95,2 %). IR spektrum (KBr tableta): 7(NH) 3 270, 3 190, 7 (CN) 2 230, 7 (C-C. ) 1 600, 1 590, 1 490,1 450, 7 (NHCS) 1 550, -1 ΛΓ Yield of 1- (4-bromophenyl) -3- (cyanophenyl) thiourea 15.8 g (95.2%). IR spectrum (KBr tablet): δ (NH) 3,270, 3,190.7 (CN) 2,230.7 (CC.) 1,600, 1,590, 1,490.1 450.7 (NHCS) 1,550.1 ΛΓ
230 cm .230 cm.
Příklad 2Example 2
2-Isothiokyanatobenzonitril (8 g, 0,05 mol) byl rozpuštěn ve 100 cm směsí dichlormethan-petrolether (1 : 1). Při teplotě 0 °C byl přikapán za míchání roztok 4-toluidinu (5,4 g, 0,05 mol) v 50 cm dichlormethanu. Po 3 hodinách reakce byl produkt odsát a promyt dichlormethanem.2-Isothiocyanatobenzonitrile (8 g, 0.05 mol) was dissolved in 100 cm 3 with dichloromethane-petroleum ether (1: 1). A solution of 4-toluidine (5.4 g, 0.05 mol) in 50 cm 3 of dichloromethane was added dropwise with stirring at 0 ° C. After 3 hours of reaction, the product was filtered off with suction and washed with dichloromethane.
Bílá krystaly, teplota tání 181 až 183 °C. <,White crystals, m.p. 181-183 ° C. <,
Výtěžek l-(4-tolyl)-3-(2-kyanfenyl)thiomočoviny 12.6 g (94 %). IR spektrum (KBr tableta): 7 (NH) 3 280, 3 190 , 7 (CN) 2 230, 7 (c>c Ar) 1 595, 1 490, 1 450, Τ’ (NHCS) 1 555, 1 230 cm1. Přiklad 3Yield of 1- (4-tolyl) -3- (2-cyanophenyl) thiourea 12.6 g (94%). IR spectrum (KBr tablet): 7 (NH) 3 280, 3 190, 7 (CN) 2 230, 7 ( c> c Ar ) 1 595, 1 490, 1 450, δ '(NHCS) 1 555, 1 230 cm 1 . Example 3
K roztoku 8 g (0,05 mol) 2-isothiokyanatobenzonitrilu ve 100 cm směsi dichlormethan-petrolether (1:1) byl při teplotě 0 °C přikapán roztok 4-anisidinu (6,2 g, 0,05 mol) v 3 . ' cm dichlormethanu. Po 2 hodinách reakce byly krystaly odsáty, promyty dichlormethanem a vysušeny.To a solution of 8 g (0.05 mol) of 2-isothiocyanatobenzonitrile in 100 cm 3 of dichloromethane-petroleum ether (1: 1) at 0 ° C was added dropwise a solution of 4-anisidine (6.2 g, 0.05 mol) in 3. cm of dichloromethane. After 2 hours of reaction, the crystals were filtered off with suction, washed with dichloromethane and dried.
Bílá krystalická látka, teplota tání 204 až 206 °C.White crystalline substance, m.p. 204-206 ° C.
Výtěžek l-(4-methoxyfenyl)-3-(2-kyanfenyl)thiomočoviny 13,6 g (96,1 %).Yield of 1- (4-methoxyphenyl) -3- (2-cyanophenyl) thiourea 13.6 g (96.1%).
IR spektrum (KBr tableta): 7 (NH) 3 250, 3 180, 7 (CN) 2 240, 7 (C1*c Ar) 1 600, 1 590, 1 460, 7 (NHCS) 1 550, 1 220 cm1.IR spectrum (KBr tablet): 7 (NH) 3250, 3180, 7 (CN) 2240, 7 (C 1 * C Ar) 1600, 1590, 1460, 7 (NHCS) 1550, 1220 cm 1 .
Příklad 4Example 4
2-Isothiokyanatobenzonitril (8 g, 0,05 mol) rozpuštěný ve 100 cm směsi dichlormethan -petrolether (1 : 1) byl při teplotě 20 °C přikapán za mícháni k emulzi obsahující ve 10 cm^ 3.5 g (0,05 mol) terč, butylaminu. Po 60 minutách míchání byl produkt odsát, promyt dichlormethanem a vysušen.2-Isothiocyanatobenzonitrile (8 g, 0.05 mol) dissolved in 100 cm 3 of dichloromethane-petroleum ether (1: 1) was added dropwise at 20 ° C with stirring to an emulsion containing in 10 cm 3 3.5 g (0.05 mol) of a target , butylamine. After stirring for 60 minutes, the product was filtered off with suction, washed with dichloromethane and dried.
yy
CS 276128 B6 2CS 276128 B6 2
Bílé krystaly, teplota táni 163 až 164 °C.White crystals, m.p. 163-164 ° C.
Výtěžek 1-terc. butyl-3-(2-kyanfenyl)thiomočoviny 9,1 g (76,1 %). IR spektrum (KBr tableta) μ (NH) 3 230, 3 190, 7 (CN) 2-220, 7 (c c Ar) 1 605, 1 585, 1 450, 7 (NHCS) 1 540, 1 205, μ (CH) 2 980, 2 880 cm1. ,Yield 1-tert. butyl 3- (2-cyanophenyl) thiourea 9.1 g (76.1%). IR spectrum (KBr tablet) μ (NH) 3 230, 3 190, 7 (CN) 2-220, 7 ( c c Ar ) 1 605, 1 585, 1 450, 7 (NHCS) 1 540, 1 205, μ (CH) 2 980, 2 880 cm -1 . ,
Příklad 5 .Example 5.
K roztoku 2-isothiokyanatobenzonitrllu (8 g, 0,05 mol) ve 100 cm směsi dichlormethan-petrolether (1 : 2) byl při teplotě 0 °C přikapán isopropylamin (2,9 g, 0,05 mol) rozpuštěný v 10 cm dichlormethanu. Po 2 hodinách reakce byl produkt odsát, promyt dichlormethanem a vysušen.To a solution of 2-isothiocyanatobenzonitrile (8 g, 0.05 mol) in 100 cm 3 of dichloromethane-petroleum ether (1: 2) at 0 ° C was added dropwise isopropylamine (2.9 g, 0.05 mol) dissolved in 10 cm 3 of dichloromethane . After 2 hours of reaction, the product was filtered off with suction, washed with dichloromethane and dried.
Bílá krystalická látka, teplota tání 156 až 158 °C.White crystalline substance, m.p. 156-158 ° C.
Výtěžek l-isopropyl-3-(2-kyanfenyl)thiomočoviny 9,8 g (90 %), IR spektrum (KBr tableta): 7(NH) 3 280, 3 190, 7 (CN) 2 240, 7 (c“c Ar) 1 600· 1 580, 1 470· (NHCS) 1 550, 1 210, 7 (CH) 2 980, 2 950 cm-1.Yield of 1-isopropyl-3- (2-cyanophenyl) thiourea 9.8 g (90%), IR spectrum (KBr tablet): 7 (NH) 3 280, 3 190, 7 (CN) 2 240, 7 ( c " C Ar) 1600 · 1 580 · 1470 (NHCS) 1550, 1210, 7 (CH) 2980, 2950 cm -1.
Příklad 6 o 2-Isothiokyanatobenzonitril (8 g, 0,05 mol) byl rozpuštěn ve 100 cm směsi dichlormethan-petrolether (1 : 1) a při teplotě 0 °C bylo přikapáno 5 g (0,05 mol) cyklohexylaminu. PoExample 6 o 2-Isothiocyanatobenzonitrile (8 g, 0.05 mol) was dissolved in 100 cm 3 of dichloromethane-petroleum ether (1: 1) and 5 g (0.05 mol) of cyclohexylamine were added dropwise at 0 ° C. After
120 minutách míchání bylo přidáno 50 cm petroletheru, produkt odsát a promyt dichlormethanem.After stirring for 120 minutes, 50 cm 3 of petroleum ether are added, the product is filtered off with suction and washed with dichloromethane.
Bílé krystaly, teplota tání 171 až 173 °C.White crystals, m.p. 171-173 ° C.
Výtěžek l-cyklohexyl-3-(2-kyanfenyl)thiomoČovlny 11,9 g (92 %). IR spektrum (KBr tableta): 7(NH) 3 280, 3 200, 7 (CN) 2 240, 7 (C»CAr) 1 600, 1 500, 1 450, 7 (NHCS) 1 560, 1 220, 7(CH) 2 950, 2 860 cm-1.Yield of 1-cyclohexyl-3- (2-cyanophenyl) thiourea 11.9 g (92%). IR spectrum (KBr tablet): δ (NH) 3,280, 3,200, 7 (CN) 2,240.7 (C 1 -C Ar ) 1,600, 1,500, 1,450.7 (NHCS) 1,560, 1,220, 7 (CH) 2 950, 2 860 cm -1 .
Příklad 7Example 7
K roztoku 8 g (0,05 mol) 2-isothiokyanatobenzonitrilu v 75 cm směsi dichlormethan-petrolether (1:1) byl přikapán při teplotě 0 °C roztok 5,4 g (0,05 mol) fenylhydrazinu 3 v 50 cm dichlormethanu. Po 60 minutách míchání byl produkt odsát, promyt dichlormethanem a vysušen.To a solution of 8 g (0.05 mol) of 2-isothiocyanatobenzonitrile in 75 cm 3 of dichloromethane-petroleum ether (1: 1) was added dropwise at 0 ° C a solution of 5.4 g (0.05 mol) of phenylhydrazine 3 in 50 cm 3 of dichloromethane. After stirring for 60 minutes, the product was filtered off with suction, washed with dichloromethane and dried.
Bílá krystalická látka, teplota tání 191 až 193 °C.White crystalline substance, m.p. 191-193 ° C.
Výtěžek l-anilino-3-(2-kyanfenyl)thiomočoviny 12,1 g (90 %). IR spektrum (KBr tableta): 7(NH) 3 300, 3 24Ó, 3 150, 7 (CN) 2 230, 7 (C=CAr) 1 600, 1 585, 1 450, 7*(NHCS) 1 540, 1 210 cm1.Yield of 1-anilino-3- (2-cyanophenyl) thiourea 12.1 g (90%). IR spectrum (KBr tablet): δ (NH) 3,300, 3,24, 3,150,7 (CN) 2,230.7 (C = C Ar ) 1,600, 1,585, 1,450.7 * (NHCS) 1,540 , 1,210 cm 1 .
, 1-Substituované 3-(2-kyanfenyl)thiomočoviny obecného vzorce I se používají jednak k syntéze Ν,Ν'-disubstituovaných, reap. N,N,N*-trisubstituovaných N-(2-kyanfenyl)guanidinO, jednak k přípravě 3-, resp. 4-eubetituovaných chinazoliná, které pro své fyziologické účinky nacházejí uplatnění zejména ve farmakologii a v zemědělství.The 1-substituted 3- (2-cyanophenyl) thioureas of the formula I are used, on the one hand, for the synthesis of Ν, Ν'-disubstituted, reap. N, N, N * -trisubstituted N- (2-cyanophenyl) guanidineO, on the one hand for the preparation of 3- and 4-eubstituted quinazolines, which for their physiological effects find application mainly in pharmacology and agriculture.
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| CS276128B6 true CS276128B6 (en) | 1992-04-15 |
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