CS266762B1 - 3-Substituted 4-Imino-1,2,3,4-tetrano-1,2,3,4-tetrahydro-quinazoline-2-thiones - Google Patents
3-Substituted 4-Imino-1,2,3,4-tetrano-1,2,3,4-tetrahydro-quinazoline-2-thiones Download PDFInfo
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Abstract
Řešení se týká 3-substlLuovanýcb 4- -lmlno-1,2,3,4-tetrahydrochlnazolín-2- -thlonú obecného vzorce I, kde R znamená 4-bromfenyl-, 4-chlorfenyí-, 4-tolyl-, 4-methoxyfenyl-, 4-hydroxyfenyl-, 4-nltrofenyl-, 3-nltrofenyl-, 2-nltrofenyI-, 4- -acatyífenyl-, ethyl-, propyl-, lsopropyl-, cyklohexyl-, 2-hydroxyethyl-, oktadecyl-, amlno-, hydroxy-, anlllnoskupinu a způsobu jejich přípravy reakcí 2-lsotbiokyanát0benzonitrilu s odpovídajícími primárními aminy při teplotě 20-80°C v organických rozpouštědlech. Látky obecného vzorce I Jsou meziprodukty pro přípravu 2,4-dlsubstltuovaných chlnazollnů, které se používají ve farmacii a v zemědělství.The solution relates to 3-substituted 4-amino-1,2,3,4-tetrahydroquinazoline-2-yl groups of general formula I, where R represents 4-bromophenyl, 4-chlorophenyl, 4-tolyl, 4-methoxyphenyl, 4-hydroxyphenyl, 4-nitrophenyl, 3-nitrophenyl, 2-nitrophenyl, 4-acetylphenyl, ethyl, propyl, isopropyl, cyclohexyl, 2-hydroxyethyl, octadecyl, amino, hydroxy, anilino groups and a method for their preparation by reacting 2-isothiocyanatobenzonitrile with corresponding primary amines at a temperature of 20-80°C in organic solvents. The compounds of general formula I are intermediates for the preparation of 2,4-disubstituted chlorobenzolines, which are used in pharmacy and agriculture.
Description
Vynález se týká 3-substltuovaných 4-lmlno-1,2,3,4-tetrabydrochInazolln-2-1hlonů obecného vzorce IThe invention relates to 3-substituted 4-imino-1,2,3,4-tetrahydrodiazinazin-2-1-rings of the general formula I
kde R znamená 4-bromfeny1-, 4-chlorfenyl-, 4-tolyl-, 4-methoxyfeny1-, 4-hydroxyfenyl-, 4-nltrofeny1-, 3-nltrof eny 1-, 2-nltrofenyl- 4-acetyIfenyl-, ethyl-, isopropyl-, propyl-, cyklohexyl-, oktadecyl-, 2-hydroxyethy1-, amino-, hydroxy-, anilInoskuplnu a způsobu jejich přípravy reakcí 2-lsothlokyanatobenzonltrilu s primárními aminy při teplotě 20Qwherein R is 4-bromophenyl-, 4-chlorophenyl-, 4-tolyl-, 4-methoxyphenyl-, 4-hydroxyphenyl-, 4-nitrophenyl-, 3-nitrophenyl-, 2-nitrophenyl-4-acetylphenyl-, ethyl -, isopropyl-, propyl-, cyclohexyl-, octadecyl-, 2-hydroxyethyl-, amino-, hydroxy-, anilino and a process for their preparation by reacting 2-isothloocyanatobenzonitrile with primary amines at 20 ° C.
-80 C v organických rozpouštědlech.-80 C in organic solvents.
Látky obecného vzorce I a způsob jejich přípravy nebyly doposud- popsány. Z literatury Je známo, že příbuzný 3-feny1-4-lmlno-l,2,3,4-tetrahydrochinazolin-2-thlon lze připravit bud adicí anthranllonltrilu na fenyllsothlokyanát v benzenovém roztoku za varu /reakční doba 20 hodin, výtěžek 53 %/ nebo 10 minutovým varem 1-feny1-3—/2-kyanfeny1/ thiomočoviny v methanolu ve výtěžku 95 % /Taylor E.C., Ravlndranathan R.V., J.Org.Chem. 27, 2622 /1962/. '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 3-phenyl-4-imino-1,2,3,4-tetrahydroquinazolin-2-thlone can be prepared either by the addition of anthranonlonyltril to phenyl isothloocyanate in boiling benzene solution (reaction time 20 hours, yield 53%)). or boiling 1-phenyl-3- (2-cyanophenyl) thiourea in methanol in 95% yield for 10 minutes [Taylor EC, Ravlndranathan RV, J.Org.Chem. 27, 2622 (1962). '
Nyní bylo nalezeno, že látky obecného vzorce I lze připravit reakcí 2-lsothiokyanatobenzonltrilu s odpovídajícími primárními aminy v organických rozpouštědlech při teplotě 20-80°C ve výtěžku 74-96 %.It has now been found that the compounds of formula I can be prepared by reacting 2-isothiocyanatobenzonitrile with the corresponding primary amines in organic solvents at 20-80 ° C in a yield of 74-96%.
Příklad 1Example 1
Směs obsahující v 60 cm^dlchlormethanu 4 g /0,025 mol/ 2-lsothiokyanatobenzonitrllu a 2 g /0,044 mol/ ethylaminu byla míchána za teploty místnosti po dobu 60 minut.A mixture containing in 4 cm 3 of dichloromethane 4 g (0.025 mol) of 2-isothiocyanatobenzonitrile and 2 g (0.044 mol) of ethylamine was stirred at room temperature for 60 minutes.
Poté byla směs vakuově zahuštěna na poloviční objem, produkt odsát, promyt dichlor-. methanem.The mixture was then concentrated in vacuo to half volume, the product filtered off with suction and washed with dichloromethane. methane.
Bílá krystalická látka, teplota táni 21O-211°C. Výtěžek 3-ethy1-4-lmlno-l,2,3,4—tetrahydrochlnazolln-2-thionu 4,9 g /95 %/.White crystalline substance, m.p. 21O-211 ° C. Yield of 3-ethyl-4-amino-1,2,3,4-tetrahydroquinazoline-2-thione 4.9 g (95%).
IR soektrum /KBr tableta/:9 /C=N/ 1 630, V /NHCS/ 1 55P, 1 225,Y/C=CAr/ 1 590, 1 470, V/NH/ 3 390, 3 250 cm-1.IR spectrum (KBr tablet): 9 / C = N / 1 630, V / NHCS / 1 55P, 1 225, Y / C = C Ar / 1 590, 1 470, V / NH / 3 390, 3 250 cm - 1 .
Příklad 2Example 2
Rozt.ok obsahující v 60 cm chloroformu 4 g /0,025 mol/ 2-lsothlokyanatobenzonltrllu a 1,5 g /0,025 mol/ Isooropylaminu byl 20 minut refluxován. Po ochlazení reakční směsi byl produkt odsát., promyt chloroformem a vysušen.A solution containing 4 g (0.025 mol) of 2-isothloocyanatobenzonitrile and 1.5 g (0.025 mol) of isooropylamine in 60 cm 3 of chloroform was refluxed for 20 minutes. After cooling the reaction mixture, the product was filtered off with suction, washed with chloroform and dried.
Bílá krystalická látka, teplota tání 259-261°C. Výtěžek 3-lsopropy1-4-lmlno-l,2,3, 4—terahydrochinazolln-2-thrlonu 5 g /91 %/.White crystalline substance, m.p. 259-261 ° C. Yield of 3-isopropyl-4-imino-1,2,3,4-terahydroquinazoline-2-trione 5 g (91%).
IR spektrum /KBr tableta/r^/ON/ 1 620,9/NHCS/ 1 550, 1' 210,^/0=^/ 1 580, 1 460, - y/NH/ 3 290, 3 20O.Y/CH/ 2 950, 2 880 cmi .IR spectrum (KBr tablet). CH / 2 950, 2 880 cmi.
Příklad 3Example 3
K roztoku 4 g /0,025 mol/ 2-lsothíokyanatobenzonltrllu v 60 cm dlchlormethanu bylo za varu prikapáno 2,5 g /0,025 mol/ cyklohexylaminu. Směs byla ponechána zvolna vychladnout na teplotu místnosti, produkt byl odsát a promyt dlchlormethanem.To a boiling solution of 4 g (0.025 mol) of 2-isothiocyanatobenzonitrile in 60 cm 3 of dichloromethane was added dropwise 2.5 g (0.025 mol) of cyclohexylamine. The mixture was allowed to cool slowly to room temperature, the product was filtered off with suction and washed with dichloromethane.
Bílé krystály, teplota tání 318 - 320°C.White crystals, m.p. 318-320 ° C.
Výtěžek 3-cyklohexy1-4-lmlno-1,2,3,4-tetrahydrochinazolln-2-thipnu 6,1 /93,8%/. IR spektrum /KBr tableta/:y /C-^/ 1 630,^ /NHCS/ 1 550, 1 220,ý /C=CAl./ 1 595, 1 500, 1 455,7 /NH/ 3 250, 3 160,7 /CH/ 2 55Q» 2 660 cm“1.Yield of 3-cyclohexyl-4-imino-1,2,3,4-tetrahydroquinazoline-2-thipine 6.1 (93.8%). IR spectrum / KBr /: y / C - ^ / 1630, ^ / NHCS / 1550, 1 220, Y / C = C Al ./ 1595, 1500, 1 455.7 / NH / 3250, 3 160.7 / CH / 2 55Q » 2 660 cm“ 1 .
Příklad 4 'Example 4 '
-------------- 3 .-------------- 3.
K roztoku oktadecylaminu /6,7 g, 0,025 mol/ ve 100 cm ethanolu byl za varu prikapáván roztok 4 g /0,025 mol/ 2-lsothlokyanatobenzonitrllu v 40 cm^chloroformu. Po 60 minutách varu byla směs ochlazena, produkt odsát a překrystalován z ethanolu /přidáno aktivní uhlí/.To a boiling solution of octadecylamine (6.7 g, 0.025 mol) in 100 cm 3 of ethanol was added dropwise a solution of 4 g (0.025 mol) of 2-isothlocyanatobenzonitrile in 40 cm 3 of chloroform. After boiling for 60 minutes, the mixture was cooled, the product filtered off with suction and recrystallized from ethanol (activated carbon added).
Bílé krystaly, teplota tání 12O-123°C.White crystals, m.p. 12O-123 ° C.
Výtěžek 3-oktadecy1-4-lmlno-l,2,3,4-tetrahydrochlnazolln-2-thlonu T,9 g /74 %/. IR spektrum /KBr tableta/: Y /C=N/ 1 625,Ý/NHCS/ 1,555, 1 220,)//C=CAr/ 1 590, 1 470, y/NH/ 3 250, 3 190,7/CH/ 2 950, 2 870 cm“1.Yield of 3-octadecyl-4-imino-1,2,3,4-tetrahydroquinazolin-2-thione T, 9 g (74%). IR spectrum / KBr /: Y / C = N / 1625, Y / NHCS / 1555, 1220,) // Ar C = C / 1590, 1470, s / NH / 3250 3 190.7 / CH / 2 950, 2 870 cm “ 1 .
Příklad 5Example 5
Směs obsahující 4 g /0,025 mol/ 2-isothiokyanatobenzonitrllu, 1,5 g /0,025 mol/ ethanolamlnu a 75 cm1 ethanolu byla míchána při teplotě 50°C po dobu 60 minut. Poté byla zahuštěna na poloviční objem, produkt odsát a promyt dlchlormethanern.A mixture containing 4 g (0.025 mol) of 2-isothiocyanatobenzonitrile, 1.5 g (0.025 mol) of ethanolamine and 75 cm 1 of ethanol was stirred at 50 ° C for 60 minutes. It was then concentrated to half volume, the product filtered off with suction and washed with dichloromethane.
Bílé krystaly, teplota tání 257-260°C.White crystals, m.p. 257-260 ° C.
Výtěžek 3-/2-hydroxyethyl/-4-lmino-I,2,3,4-tetrahydrochinazolln-2—thionu 4,5 g /83 %/. IR spektrum /KBr tableta/: V/C=N/ 1 530,7/NHCS/ 1 550, I 205 , V/C=CAr/ 1 590,1 500,1'470 7/NH/ 3 300, 3 200,y/CH/ 2 970, 2 870,y/OH/ 3 400,7/0-0/ 1 040 cm“1.Yield of 3- (2-hydroxyethyl) -4-imino-1,2,3,4-tetrahydroquinazoline-2-thione 4.5 g (83%). IR spectrum (KBr tablet): V / C = N / 1 530.7 / NHCS / 1 550, I 205, V / C = C A r / 1 590.1 500, 1470 7 / NH / 3 300, 3,200, y / CH / 2,970, 2,870, y / OH / 3,400.7 / 0-0 / 1,040 cm “ 1 .
Příklad 6Example 6
Hydroxylamonlum chlorid /1,8 g, 0,025 mol/ byl rozpuštěn v 50 cm methanolu. K roztoku byl přidán 1 g /0,025 mol/ hydroxidu sodného. Vzniklá suspenze byla za teploty místnosti filtrována do roztoku 2-isothiokyanatobenzonitrllu /4 g, 0,025 mol/ v 25 cm1 methanolu a směs míchána 30 minut.. Poté byla suspenze zahuštěna na poloviční objem, krystaly odsáty, promyty chloroformem a vysušeny ve vakuu.Hydroxylammonium chloride (1.8 g, 0.025 mol) was dissolved in 50 cm 3 of methanol. 1 g (0.025 mol) of sodium hydroxide was added to the solution. The resulting suspension was filtered at room temperature into a solution of 2-isothiocyanatobenzonitrile (4 g, 0.025 mol) in 25 cm 3 of methanol and stirred for 30 minutes. The suspension was then concentrated to half volume, the crystals filtered off with suction, washed with chloroform and dried in vacuo.
Bílá krystalická látka, teplota tání 219-221°C.White crystalline substance, m.p. 219-221 ° C.
Výtěžek 3-hydroxy-4-lmlno-l,2,3,4-tetrahydrQChinazolln-2-thlonu 4,1 g /84,8 %/. IR spektrum /KBr tableta/:V /C=N/ 1 640,7/NHCS/ 1 550, 1 230,7/C=CAj./ 1 595, 1 470, ý/NH 3 300, 3 200,7/OH/ 3 '550 cm“1. .Yield of 3-hydroxy-4-imino-1,2,3,4-tetrahydroquinazolin-2-thione 4.1 g (84.8%). IR spectrum (KBr tablet): V / C = N / 1,640.7 / NHCS / 1,550, 1,230.7 / C = C Aj . / 1,595, 1,470, NH / 3,300, 3,200.7 / OH / 3 '550 cm “ 1 . .
Příklad 7Example 7
V 50 cm^ chloroformu byly rozpuštěny 4 g /0,025 mol/ 2-isothiokyanatobenzonitrllu. K roztoku byl za teploty místnosti přlkapán v průběhu 10 minut 100% hydrazinhydrát /1,3 g, 0,025 mol/ rozpuštěný v 10 cm1 methanolu. Směs byla míchána 30 minut, potě zahuštěna na poloviční objem, produkt, odsát, promyt methanolem a vysušen ve vakuu.4 g (0.025 mol) of 2-isothiocyanatobenzonitrile were dissolved in 50 cm 3 of chloroform. 100% hydrazine hydrate (1.3 g, 0.025 mol) dissolved in 10 cm 1 of methanol was added dropwise to the solution over 10 minutes at room temperature. The mixture was stirred for 30 minutes, then concentrated to half volume, the product filtered off with suction, washed with methanol and dried in vacuo.
Bílé krystaly, teplota tání 219~221°C.White crystals, m.p. 219 ~ 221 ° C.
Výtěžek 3-amlno-4-imlno-l,2,3,4-tetrahydrochlnazolln-2-thlonu 3,9 g /81,1 %/. ·Yield of 3-amino-4-imino-1,2,3,4-tetrahydroquinazolin-2-thione 3.9 g (81.1%). ·
IR spektrum /KBr tableta/: y/C=N/ 1 640,7”/ΝΗε5/ 1 560, 1 225,7/C=CAr/ 1 600, 1 455, 7/NH/ 3 400, 3 250, 3 200 cm“1.IR spectrum (KBr tablet): γ / C = N / 1,640.7 ”/ εε5 / 1,560, 1,225.7 / C = C Ar / 1,600, 1,455.7 / NH / 3,400, 3,250. 3 200 cm “ 1 .
Příklad 8Example 8
K roztoku 4 g /0,025 mol/ 2-lsothlokyanatobenzonltrllu v 50 cm1 dlchlormethanu byl za varu přlkapán roztok 2,7 g /0,025 mol/ fenyIhydrazinu v 20 cm^dichlormethanu.To a boiling solution of 4 g (0.025 mol) of 2-isothloocyanatobenzonitrile in 50 cm 3 of dichloromethane was added dropwise a solution of 2.7 g (0.025 mol) of phenylhydrazine in 20 cm 3 of dichloromethane.
- 2 266762 Po 20 minutách varu byla směs ochlazena na teplotu místnosti, produkt odsát, promyt dichlormethanem a vysušen.After boiling for 20 minutes, the mixture was cooled to room temperature, the product was filtered off with suction, washed with dichloromethane and dried.
Bílé krystaly, teplota tání 209-211°C.'White crystals, m.p. 209-211 ° C.
Výtěžek 3-anilino~4-lmlno-l,2,3,4-tetrahydrochinazolin-2-thionu 6,2 g /92,5 %/. IR spektrum /KBr tableta/: γ /C=N/ 1 640,Ϋ /NHCS/ 1 550, 1 210,^/0=0^/ 1 600, 1 500, 1 450,V /NH/ 3 300, 3 260, 3 190 cm1.Yield of 3-anilino-4-imino-1,2,3,4-tetrahydroquinazoline-2-thione 6.2 g (92.5%). IR spectrum (KBr tablet): γ / C = N / 1 640, Ϋ / NHCS / 1 550, 1 210, ^ / 0 = 0 ^ / 1 600, 1 500, 1 450, V / NH / 3 300, 3 260, 3 190 cm 1 .
Příklad 9.Example 9.
K roztoku 4-aminoacetofenonu /3,4 g, 0,025 mol/ v 50 cm ethanolu byl za teploty .2 místnosti přlkapán roztek 2-lsothlokyanatobenzonitrllu /4 g, 0,025 mol/ v 30 cm dichlormethanu. Směs byla míchána za teploty místnosti 10 hodin. Produkt byl odsát, promyt dichlormethanem a vysušen.To a solution of 4-aminoacetophenone (3.4 g, 0.025 mol) in 50 cm 3 of ethanol at room temperature was added dropwise a solution of 2-isothlocyanatobenzonitrile (4 g, 0.025 mol) in 30 cm 3 of dichloromethane. The mixture was stirred at room temperature for 10 hours. The product was filtered off with suction, washed with dichloromethane and dried.
Bílé krystaly, teplota tání 210-212°C.White crystals, m.p. 210-212 ° C.
Výtěžek 3-/4-acetylfenyl/-4-imino-l,2,3,4-tetrahydrochinazolin-2-tbionu 6 g /61 %/. IR spektrum /KBr tableta/: /C=N/ 1 645, /NHCS/ 1 550, 1 210, /C=CA / 1 600, 1 590, 1 490, /NH/ 3 390, 3 250, /OH/ 2 960, 2 870, /C=0/ 1 675 cm1.Yield of 3- (4-acetylphenyl) -4-imino-1,2,3,4-tetrahydroquinazoline-2-thione 6 g (61%). IR spectrum (KBr tablet): / C = N / 1 645, / NHCS / 1 550, 1 210, / C = C A / 1 600, 1 590, 1 490, / NH / 3 390, 3 250, / OH / 2 960, 2 870, / C = 0/1 675 cm 1 .
Příklad 10 ' 2 f Example 10 '2 f
K roztoku 4-nltroanlllnu /3,4 g, 0,025 mol/ v 50 cm ethanolu byl za varu přlkapán 3 ' roztok 4 g /0,025 mol/ 2-lsothlokyanatobenzonitrllu ve 20 cm dichlormethanu. Po 30 minutách varu byl roztok zahuštěn na poloviční objem, produkt odsát a vysušen.To a boiling solution of 4-nitroaniline (3.4 g, 0.025 mol) in 50 cm 3 of ethanol was added dropwise a 3 'solution of 4 g (0.025 mol) of 2-isothloocyanatobenzonitrile in 20 cm 3 of dichloromethane. After boiling for 30 minutes, the solution was concentrated to half volume, the product was filtered off with suction and dried.
Nažloutlé krystaly, (eplota tání 270-272°C. Výtěžek 3-/4-nltrofenyl/-4-lmino-l,2,3,4-tetrahydrochinazolin-2-thlonu 6,3 g /85,1 %/. IR spektrum /KBr tableta/:^/C=N/ 1 625,7 /NHCS/ 1 550, 1 230,V/C=CAr/ 1 590, 1 490, 1 460,V /NH/ 3 290, 3 120,7/N02/ 1 530, 1 340 cm1.Yellowish crystals, (m.p. 270-272 ° C. Yield of 3- (4-nitrophenyl) -4-amino-1,2,3,4-tetrahydroquinazolin-2-thlone 6.3 g (85.1%). IR spectrum (KBr tablet): ^ / C = N / 1 625.7 / NHCS / 1 550, 1 230, V / C = C Ar / 1 590, 1 490, 1 460, V / NH / 3 290, 3 120 7 / N0 2/1 530 1340 cm 1st
Příklad 11Example 11
Směs 4 g /0,025 mol/ 2-isothiokyanatobenzonitrilu, 3,4 g /0,025 mol/ 3~nitroanilinu a 50 cm ethanolu byla míchána 12 hodin za teploty místnosti a poté krátce povařena. Ochlazením směsi na cca 5°C byly vyloučeny krystaly, ty odsáty, promyty ethanolem a vysušeny ve vakuu.A mixture of 4 g (0.025 mol) of 2-isothiocyanatobenzonitrile, 3.4 g (0.025 mol) of 3-nitroaniline and 50 cm 3 of ethanol was stirred for 12 hours at room temperature and then boiled briefly. By cooling the mixture to about 5 [deg.] C., the crystals precipitated, which were filtered off with suction, washed with ethanol and dried in vacuo.
Nažloutlé krystaly, teplota tání 318-320°C.Yellowish crystals, m.p. 318-320 ° C.
Výtěžek 3-/3-nitrofenyl/-4-imino-l,2,3,4-tetrahydrochinazolin-2^thinu 6,5 g /87,8 %/. IR spektrum /KBr tableta/:7/C=N/ 1 630, } /NHCS/ 1 550, 1 220,7 /C=CAr/ 1 600, 1 490, γ /NH/ 3 260, 3 170,V/NOj/ 1 530, 1 350 cm1.Yield of 3- (3-nitrophenyl) -4-imino-1,2,3,4-tetrahydroquinazolin-2-thione 6.5 g (87.8%). IR spectrum (KBr tablet): 7 / C = N / 1 630,} / NHCS / 1 550, 1 220.7 / C = C Ar / 1 600, 1 490, γ / NH / 3 260, 3 170, V / NOj / 1 530, 1 350 cm 1 .
Příklad 12Example 12
K roztoku 2-lsothlokyanatobenzonitrilu /4 g, 0,025 mol/ v 60 cm^ chloroformu byl 2 za varu přikapán roztok 3,1 g /0,025 mol/ p-anisidinu v 40 cm methanolu. Po 10 minutách varu byla směs ochlazena na teplotu místnost.!, produkt odsát a vysušen.To a solution of 2-isothloocyanatobenzonitrile (4 g, 0.025 mol) in 60 cm 3 of chloroform was added dropwise a boiling solution of 3.1 g (0.025 mol) of p-anisidine in 40 cm 3 of methanol. After boiling for 10 minutes, the mixture was cooled to room temperature, the product was filtered off with suction and dried.
Bílé krystaly, teplota tání 281-282°C.White crystals, m.p. 281-282 ° C.
Výtěžek 3-/4-methoxyfenyl/-4-imino-l,2,3,^ctetrahydrcrchlnazolln-2-thlonu 6,3 g /88,7 %/. IR spektrum /KBr table ta / :V/C=N/, 1 640.Y/NHCS/ 1 550, 1 210, Ϋ/C=CAl./ 1 600, 1 490, y /CH/ 2 970, 2880,7/COC/ 1 020 cm'1.Yield of 3- (4-methoxyphenyl) -4-imino-1,2,3,4-tetrahydroquinazolin-2-thione 6.3 g (88.7%). IR spectrum (KBr table ta): V / C = N /, 1 640.Y / NHCS / 1 550, 1 210, Ϋ / C = C Al ./ 1 600, 1 490, y / CH / 2 970, 2880 , 7 / COC / 1 020 cm ' 1 .
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Příklad 13 . τExample 13. τ
K roztoku 4 g /0,025 mol/ 2-lsothiokyanatobenzonitrllu v 50 cm chloroformu byl za 3 varu přikapán roztok 2,7 g /0,025 mol/ p-toluldlnu v 20 cm methanolu. Po 10 minutách varu byla směs ochlazena, produkt odsát, promyt chloroformem a vysušen.To a solution of 4 g (0.025 mol) of 2-isothiocyanatobenzonitrile in 50 cm 3 of chloroform was added dropwise a solution of 2.7 g (0.025 mol) of p-tolylene in 20 cm 3 of methanol under boiling. After boiling for 10 minutes, the mixture was cooled, the product was filtered off with suction, washed with chloroform and dried.
Bílé krystaly, teplota tání 299-301°C.White crystals, m.p. 299-301 ° C.
Výtěžek 3-/4-toIyl/-4-lmlno-l,2,3,4-tetrahydrochinazolln-2-tiony 6,1 g /91 %/· IR spektrum /KBr tableta/: p7c=N/ 1 640,V/NHCS/ 1 555, 1 210,//C=CAr/ 1 600, 1 490, Ϋ/ΝΗ/ 3 280, 3 180, V/CH/ 2 960, 2 880 cm1.Yield of 3- (4-tolyl) -4-imino-1,2,3,4-tetrahydroquinazolin-2-thione 6.1 g (91%) IR spectrum (KBr tablet): p7c = N / 1640, V / NHCS / 1 555, 1 210, // C = C Ar / 1 600, 1 490, Ϋ / ΝΗ / 3 280, 3 180, V / CH / 2 960, 2 880 cm 1 .
Příklad 14 'Example 14 '
Směs pbsahující 4 g /0,025 mol/ 2-lsothlokyanatobenzonltrllu, 4,3 /0,025 mol/ 4-bromanlllnu a 100 cm1 chloroformu byla refluxována 60 mtnut. Po ochlazení byl produkt odsát, promyt chloroformem a vysušen.A mixture of 4 g (0.025 mol) of 2-isothloocyanatobenzonitrile, 4.3 (0.025 mol) of 4-bromoaniline and 100 cm 3 of chloroform was refluxed for 60 minutes. After cooling, the product was filtered off with suction, washed with chloroform and dried.
Bílé krystaly, teplota tání 275-278°C.White crystals, m.p. 275-278 ° C.
Výtěžek 3-/4-bromfeny1/—4-imlno-l,2,3,4-tetrahydrochlnazolin-2^ thionu 8 g /96 %/.Yield of 3- (4-bromophenyl) -4-imino-1,2,3,4-tetrahydroquinazoline-2-thione 8 g (96%).
JR spektrum /KBr tableta/: //C=N/ 1 640,V/NHCS 1 540, 1 210,y/C=CAr/ 1 585, 1 495, V /NH/ 3 280, 3 140 cm1.JR spectrum (KBr tablet): // C = N / 1 640, V / NHCS 1 540, 1 210, y / C = C Ar / 1 585, 1 495, V / NH / 3 280, 3 140 cm -1 .
3-Substituované 4-imlno-l,2,3-tetrahydrochlnazolin-2-thlony obecného vzorce I Jsou meziprodukty pro přípravu 2,4-disubstltuovaných chlnazollnu, které se používají ve farmacii a v zemědělství.3-Substituted 4-imino-1,2,3-tetrahydroquinazolin-2-thlones of formula I They are intermediates for the preparation of 2,4-disubstituted chlorazolines which are used in pharmacy and agriculture.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884151A CS266762B1 (en) | 1988-06-15 | 1988-06-15 | 3-Substituted 4-Imino-1,2,3,4-tetrano-1,2,3,4-tetrahydro-quinazoline-2-thiones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS884151A CS266762B1 (en) | 1988-06-15 | 1988-06-15 | 3-Substituted 4-Imino-1,2,3,4-tetrano-1,2,3,4-tetrahydro-quinazoline-2-thiones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS415188A1 CS415188A1 (en) | 1989-04-14 |
| CS266762B1 true CS266762B1 (en) | 1990-01-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS884151A CS266762B1 (en) | 1988-06-15 | 1988-06-15 | 3-Substituted 4-Imino-1,2,3,4-tetrano-1,2,3,4-tetrahydro-quinazoline-2-thiones |
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| CS (1) | CS266762B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017051251A1 (en) * | 2015-09-25 | 2017-03-30 | Ludwig Institute For Cancer Research Ltd | 3-hydroxy-quinazoline-2,4-dione derivatives and their use as nuclease modulators |
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1988
- 1988-06-15 CS CS884151A patent/CS266762B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017051251A1 (en) * | 2015-09-25 | 2017-03-30 | Ludwig Institute For Cancer Research Ltd | 3-hydroxy-quinazoline-2,4-dione derivatives and their use as nuclease modulators |
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| Publication number | Publication date |
|---|---|
| CS415188A1 (en) | 1989-04-14 |
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