CS200101B1 - Substituted 0-/5-pyrimidinyl/thiocarbamates and process for preparing them - Google Patents
Substituted 0-/5-pyrimidinyl/thiocarbamates and process for preparing them Download PDFInfo
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- CS200101B1 CS200101B1 CS232677A CS232677A CS200101B1 CS 200101 B1 CS200101 B1 CS 200101B1 CS 232677 A CS232677 A CS 232677A CS 232677 A CS232677 A CS 232677A CS 200101 B1 CS200101 B1 CS 200101B1
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- pyrimidinyl
- methylthio
- methyl
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- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 title claims description 3
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- -1 polymethylene chain Polymers 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- HUFSWRZCZOSTQR-UHFFFAOYSA-N 2-(2-methylpropylsulfanyl)pyrimidin-5-ol Chemical compound CC(C)CSC1=NC=C(O)C=N1 HUFSWRZCZOSTQR-UHFFFAOYSA-N 0.000 description 1
- VVTBLRLLKIDVKB-UHFFFAOYSA-N 2-methylsulfanylpyrimidin-5-ol Chemical compound CSC1=NC=C(O)C=N1 VVTBLRLLKIDVKB-UHFFFAOYSA-N 0.000 description 1
- WFGYSQDPURFIFL-UHFFFAOYSA-N 3-chloro-n-methylaniline Chemical compound CNC1=CC=CC(Cl)=C1 WFGYSQDPURFIFL-UHFFFAOYSA-N 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241001480036 Epidermophyton floccosum Species 0.000 description 1
- 241001480000 Microsporum audouinii Species 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical class CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LTXJLQINBYSQFU-UHFFFAOYSA-N pyrimidin-5-ol Chemical compound OC1=CN=CN=C1 LTXJLQINBYSQFU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
(54) Substituované 0^ ( 5-pyrlaldlnyl)thiokarbamáty způsob Jejich výroby(54) Substituted O - (5-pyrrolidinyl) thiocarbamates A process for their preparation
Vynález ze týká substituovaných 0-(5-pyrimidinyl) thiokerbamátů obecného vzorce I «I <The invention relates to substituted O- (5-pyrimidinyl) thiokerbamates of the general formula I-I
*3 (I) ve kterém R^ značí alkylthioskupinu s 1 až 4 atomy uhlíku, Rg alkyl s 1 až 4 atomy uhlíku • R^ alkyl a 1 až 4 atomy uhlíku nebo fenyl, popřípadě substituovaný jedním nebo dvěma atomy halogenu, zejména chloru, jednou nebo dvěma methyl- nebo methoxy- skupinami, nebo substituenty Rg β Rj spolu spojeny tvoří čtyř až šestičlenný polymethylenový řetězec, kterýýmůže být přerušen jedním atomem kyslíku, síry nebo dusíku. Vynélez se týká rovněž způsobu výroby látek obecného vzorce I.* 3 (I) wherein R 1 represents C 1 -C 4 alkylthio, R 4 C 1 -C 4 alkyl, R 4 alkyl and C 1 -C 4 alkyl or phenyl optionally substituted by one or two halogen atoms, especially chlorine, one or two methyl or methoxy groups, or the substituents Rg-Rj, taken together, form a four to six-membered polymethylene chain which may be interrupted by one oxygen, sulfur or nitrogen atom. The invention also relates to a process for the preparation of compounds of the formula I.
Substituované ó (5-pyrimidinyl) thiokarbamáty obeoného vzorce I jsou nové dosud nepopsané sloučeniny, u kterých byla zjištěna in vitro významné antimykotická účinnost proti různým dermatofytům, jak vyplývá z následující tabulky:The substituted δ (5-pyrimidinyl) thiocarbamates of the formula I are novel hitherto undescribed compounds which have been found to have significant antifungal activity against various dermatophytes in vitro, as shown in the following table:
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Antifungální účinnoet popisovaných látek vyjádřené minimální inhibiční koncentrací /Ug/mlThe antifungal efficacy of the disclosed compounds, expressed as a minimum inhibitory concentration / µg / ml
0-(2-Methylthio-5-pyrimidinyl)-N-methyl-N-(3,5-dichlorfenyl)thiokarba-O- (2-Methylthio-5-pyrimidinyl) -N-methyl-N- (3,5-dichlorophenyl) thiocarb-
Testované mikroorganismy jTested microorganisms j
TM Triohophyton mentagrophytes, TR Jric,hophyton rubrum, TV ®riohophyton verrucosum, TSchTM Triohophyton Mentagrophytes, TR Jric, Hophyton Rubrum, TV ®riohophyton verrucosum, TSch
Triohophyton sohoenleinii, MG Nicřůsporum gypseum, MA Microsporum audouinii, MG Miorosporum canla, EF Epidermophyton floccosum.Triohophyton sohoenleinii, MG Nicopsis gypseum, MA Microsporum audouinii, MG Miorosporum canla, EF Epidermophyton floccosum.
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Podle vynálezu ee látky obecného vzorce I mohou připravovat tak, že se na o/Ó-bis-(5-pyrimidinyl)thiokarbonát obecného vzorce IIAccording to the invention, the compounds of the formula I can be prepared by converting to the ω-bis (5-pyrimidinyl) thiocarbonate of the formula II
ve kterém R^ značí totéž co· ve vzorci I, působí sekundárním aminem obecného vzorce III /R3in which R1 denotes the same as in formula I, acts with a secondary amine of formula III / R3
HN \ (III) R2 ve kterém Rg a R^ značí totéž co ve vzorci I, v prostředí vody nebo netečného organického rozpouštědla, například ethanolu, acetonu, dioxanu, diidopropyletheru nebo dimethylsulfoxidu, při teplotě 0 až 100 °C, s výhodou 10 až 50 °C.HN 1 (III) R 2 in which R g and R 2 denote the same as in formula I, in a water or inert organic solvent such as ethanol, acetone, dioxane, diidopropyl ether or dimethylsulfoxide, at a temperature of 0 to 100 ° C, preferably 10 to 50 ° C.
Při provedení způsobu podle vynálezu se zpravidla postupuje tak, že se do roztoku sekundárního aminu obecného vzorce 111 ve zvoleném rozpouštědle vnáěí thiokarbonát obecného vzorce H a reakční aměs se nechá buď stát při teplotě místnosti ( v případě silně bazických alifatických aminů nebo heterocyklických bází, jako piperidinu, morfolinu, N-methylpiperazinu apod.) nebo se reakční směs zahřívá, popřípadě vaří, což je nutné v případě slabých bází, jako jsou N-alkylaniliny. Při této reakci se uvolní 1 mol příslušného 5-hydroxypyrimidinu, který lze po izolaci thiokarbamátu obecného vzorce I snadno regenerovat z matečného louhu a použít znovu k přípravě výchozího thiokarbonátu obecného vzorce II.Typically, a thiocarbonate of formula (H) is introduced into a solution of the secondary amine (111) in the selected solvent and the reaction mixture is allowed to either stand at room temperature (in the case of strongly basic aliphatic amines or heterocyclic bases such as piperidine). , morpholine, N-methylpiperazine, and the like) or the reaction mixture is heated or boiled as necessary in the case of weak bases such as N-alkylanilines. In this reaction, 1 mole of the corresponding 5-hydroxypyrimidine is liberated, which, after isolation of the thiocarbamate of formula I, can easily be regenerated from the mother liquor and reused to prepare the starting thiocarbonate of formula II.
Podrobnosti o způsobu přípravy nových látek obecného vzorce I, jakož i meziproduktů, pokud jejich příprava není z literatury známá, jsou uvedeny v následujících příkladech provedení.Details of the process for the preparation of the novel compounds of the formula I as well as the intermediates, if their preparation is not known from the literature, are given in the following examples.
Příklady provedení Příklad 1EXAMPLES Example 1
Do roztoku 77,0 g thiofosgenu v 500 ml chloroformu se při teplotě pod 30 °C přikape za míchání roztok 91,0 g 2-methylthio-5-hydroxypyrimidinu ve 48,5 ml 5%ního roztoku hydroxidu sodného, ^ak se reakční směs zahřeje krátce k varu pod zpětným chladičem. Po vychladnutí se vyloučená krystalická látka obsahuje a promyje vodou a acetonem, žíská se 50,0 g surového 0,*0-bis-(2-í>ethyl)-thio-5-pyrimidinyl)thiokarbonátu s b.t. 168 až 169,5 °C (tetrachlormethan).A solution of 91.0 g of 2-methylthio-5-hydroxypyrimidine in 48.5 ml of 5% sodium hydroxide solution is added dropwise with stirring to a solution of 77.0 g of thiophosgene in 500 ml of chloroform at a temperature below 30 [deg.] C. Heat briefly to reflux. After cooling, the precipitated crystalline solid was washed with water and acetone to give 50.0 g of crude O, O-bis- (2-ethyl) -thio-5-pyrimidinyl) thiocarbonate with m.p. 168 DEG-169.5 DEG C. (carbon tetrachloride).
Analogicky se z thiofosgenu a 2-isobutylthio-5-hydroxy-pyrimidinu připraví 0,0-bis-(2-ieobutylthio-5-pyrimidifiyl) thiokarbonát s b.t. 98 až 101 °C (ethanol).Analogously prepared from thiophosgene and 2-isobutylthio-5-hydroxy-pyrimidine is O-bis- (2-isobutylthio-5-pyrimidinyl) thiocarbonate with m.p. 98 DEG-101 DEG C. (ethanol).
Příklad 2Example 2
Do roztoku 8,7 g morfinu ve 150 ml acetonu se při teplotě 0 až 10 °C vnese po částech 32,6 g 0,'0-bis-(2-methyrthio-5-pyrimidinyl)thiokarbonátu a směs se míchá 2 h při teplotě místnosti. ťak se reakční směs nalije do 1000 ml studené vody, vyloučený produkt se odsaje a promyje vodou. &íská se 25,0 g 0-(2-methylthio-5-pyrimidinyl)-NTN-(3-oxapentamethylen)thiokarbamátu s b.t. 14& až 148,5 °C (ethanol).To a solution of 8.7 g of morphine in 150 ml of acetone at 0-10 ° C was added portionwise 32.6 g of O, O-bis- (2-methylthio-5-pyrimidinyl) thiocarbonate, and the mixture was stirred for 2 h at room temperature. room temperature. When the reaction mixture is poured into 1000 ml of cold water, the precipitated product is filtered off with suction and washed with water. & Iška 25.0 g of 0- (2-methylthio-5-pyrimidinyl) -N ' N- (3-oxapentamethylene) thiocarbamate & Bt 14 to 148,5 ° C (ethanol).
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Analogicky se z 0,'Ó-bis-(2-mfethylthio-5-pyrimidinyl)thiokarbonátu a příslušných a příslušných sekundárních aminů připraví tyto sloučeniny sIn analogy, these compounds are prepared from O, N-bis- (2-methylthio-5-pyrimidinyl) thiocarbonate and the corresponding and corresponding secondary amines.
0Í(2-methýlthio-5-pyrimidinyl)-N,N-dimethylthiokarbamát s b.t. 100 až 101 °C (voda), 0-(2-methylthio-5-pyrimidinyl)-N,N-pentamethylenthiokarbamát s b.t. 70,5 až 71,5 °C (60%ní ethanol),N- (2-methylthio-5-pyrimidinyl) -N, N-dimethylthiocarbamate with m.p. 100-101 ° C (water), O- (2-methylthio-5-pyrimidinyl) -N, N-pentamethylene thiocarbamate, m.p. 70.5 to 71.5 ° C (60% ethanol),
OÍ(2-methylthio-5-pyromidinyl)-N,N-(3-thiapentamethylen) thiokarbamát s b.t. 99,5 až 100,5 °C (60%ni ethanol), *N- (2-methylthio-5-pyromidinyl) -N, N- (3-thiapentamethylene) thiocarbamate with m.p. 99.5 to 100.5 ° C (60% ni ethanol), *
0_(2-methylthio-5-pyrimidinyl)-N,N-(3-methyl-3-azapentamethylen)thiokarbamát s b.t. 128 až 129 °C (30%ní methanol).O - (2-methylthio-5-pyrimidinyl) -N, N- (3-methyl-3-azapentamethylene) thiocarbamate with m.p. 128 DEG-129 DEG C. (30% methanol).
Příklad 3Example 3
Do roztoku 12,9 g di-n-butylaminu ve 15Ó ml acetonu se při teplotě 0 až 10 °C vnese po částech 32,6 g 0,z0-bis-(2-methylthio-5-pyrimidinyl) thiokarbonátu a směs se míchá 2,5 h při teplotě místnosti. Pak ae reakční směs nalije do 1000 ml studené vody a produkt se extrahuje 2x po 400 ml etheru. Po vysušení etheriokého extraktu ee ether odpaří a olejovitý odparek se čistí destilací. Líská se 20,0 g Ó-(2-methylthio-5-pyrimidinyl)-N,N-di-n-butylthiokarbamátu s b.v. 183 až 186 °C/107 Pa.To a solution of 12.9 g of di-n-butylamine in 15O mL of acetone at 0 DEG to 10 DEG C. was added portionwise 32.6 g 0, 0-bis- (2-methylthio-5-pyrimidinyl) thiocarbonate, and the mixture Stir 2.5 h at room temperature. The reaction mixture was poured into 1000 ml of cold water and the product was extracted twice with 400 ml of ether each time. After drying the ether extract, the ether was evaporated and the oily residue was purified by distillation. 20.0 g of O- (2-methylthio-5-pyrimidinyl) -N, N-di-n-butylthiocarbamate having a bp of 183-186 DEG C./0.7 mbar were obtained.
Příklad 4Example 4
Do roztoku 14,2 g N-methyl-m-chloranilinu ve 200 ml acetonu se při teplotě 0 až 20 °C vnese po malých dávkách za míchání 32,6 g 0,'oíbis(2-methylthio-5-pyrimidinyl)thiokarbonátu a smě· se zvolna zahřeje k varu pod zpětným chladičem. Po 1 1/2 h se reakční směs ochladí a nalije do 1000 ml studené vody. Vyloučený surový OÍ(2-methylthio-5-pyrimidynil)-N-methyl-N-m-ohlo3> fenylthiokarbamát se odsaje a promyje vodou. Líská se 8,1 g látky a b.t. 93 až 95 °C (ethanol).To a solution of 14.2 g of N-methyl-m-chloroaniline in 200 ml of acetone at 0 DEG to 20 DEG C. is added in small portions with stirring 32.6 g of O, O-bis (2-methylthio-5-pyrimidinyl) thiocarbonate and the mixture slowly warms to reflux. After 1 1/2 h, the reaction mixture was cooled and poured into 1000 mL cold water. The precipitated crude O (2-methylthio-5-pyrimidynil) -N-methyl-N-m-halophenylthiocarbamate is filtered off with suction and washed with water. 8.1 g of compound are obtained and m.p. 93-95 ° C (ethanol).
Analogicky se z O,'oíbis-(2-methylthio-5-pyrimidinyl)-thiokarbožátu, resp. 0'oíbis-(2-isobutylthio-5-pyrimidinyl)-thiokarbonátu a příslušnýmh N-methylanilinů připraví tyto sloučeniny»Analogously from O, O-bis (2-methylthio-5-pyrimidinyl) thiocarboxylate, respectively. O-bis (2-isobutylthio-5-pyrimidinyl) thiocarbonate and the corresponding N-methylanilines will prepare these compounds »
OÍ(2-methylthio-5-pyrimidinyl)-N-methyl-N-fenylthiokarbamát β b.t.157,5 až 158 °C(ethanol), 0—(2methylthio—5—pyrimidinyl)—N—methyl—N—3,4—dichlorfenyl—thiokarbamát s b.t. 122,5 až 123 °C (90%ní ethanol),O (2-methylthio-5-pyrimidinyl) -N-methyl-N-phenylthiocarbamate βbt 157.5-158 ° C (ethanol), O- (2-methylthio-5-pyrimidinyl) -N-methyl-N-3,4 —Dichlorophenyl thiocarbamate with bt 122.5 to 123 ° C (90% ethanol),
OÍ(2-methylthio-5-pyrimidyl)-N-methyl-R-3,5-dichlorfenylthiokarbamát s b.t.160 až 172 °C (ethanol),O (2-methylthio-5-pyrimidyl) -N-methyl-R-3,5-dichlorophenylthiocarbamate, m.p. 160-172 ° C (ethanol),
OÍ(2-methylthio-5-pyrimidinyl)-N-methyl-N-methyl-N-m-tolylthiokarbamát a b.t. 112 až 114 °C (ethanol),N- (2-methylthio-5-pyrimidinyl) -N-methyl-N-methyl-N-m-tolylthiocarbamate and m.p. 112-114 ° C (ethanol),
OÍ(2-methylthio-5-pyrimidinyl)-N-methyl-N-3,5-dimethylfenyl-thiokarbamát β b.t. 147,5 až 149 °C (85% ethanol),O (2-methylthio-5-pyrimidinyl) -N-methyl-N-3,5-dimethylphenylthiocarbamate β m.p. 147.5-149 ° C (85% ethanol),
OÍ(2-methylthio-5-pyrimidinyl)-N-methyl-N-p-methoxyfenylthiokarbamát s b.t. 102,5 až 103 °C (80%ní ethanol),N- (2-methylthio-5-pyrimidinyl) -N-methyl-N-p-methoxyphenylthiocarbamate with m.p. 102.5 to 103 ° C (80% ethanol),
0Í(2-methylthio-5-pyrimidinyl)-N-methyl-N-3,4-dimethylfenylthiokarbamát s b.t. 115,5 až 117 °C (90%ní ethanol),N- (2-methylthio-5-pyrimidinyl) -N-methyl-N-3,4-dimethylphenylthiocarbamate with m.p. 115.5-117 ° C (90% ethanol),
0Í(2-methylthio-5-pyrimidinyl)-N-methyl-N-p-tolylthiokarbamát β b.t. 109 až 111 °C(ethanol),N- (2-methylthio-5-pyrimidinyl) -N-methyl-N-p-tolylthiocarbamate β m.p. 109-111 ° C (ethanol),
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0—(2-methylthio-5-pyrimidinyl)-N-methyl-N-p-chlorfenylthiokarbamát β b.t. 143,5 až 145 °C (70%ní ethanol),O- (2-methylthio-5-pyrimidinyl) -N-methyl-N-p-chlorophenylthiocarbamate β m.p. 143.5-145 ° C (70% ethanol),
OÍ(2-isobutylthie-5-pyrimidinyl)-N-methyl-N-m-tolylthiokarbamát β b.t. 62 ei 65 °C (tetrachlormethan),N- (2-isobutylthie-5-pyrimidinyl) -N-methyl-N-m-tolylthiocarbamate β m.p. 62 ei 65 ° C (carbon tetrachloride),
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS232677A CS200101B1 (en) | 1977-04-07 | 1977-04-07 | Substituted 0-/5-pyrimidinyl/thiocarbamates and process for preparing them |
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| CS232677A CS200101B1 (en) | 1977-04-07 | 1977-04-07 | Substituted 0-/5-pyrimidinyl/thiocarbamates and process for preparing them |
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| CS200101B1 true CS200101B1 (en) | 1980-08-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS232677A CS200101B1 (en) | 1977-04-07 | 1977-04-07 | Substituted 0-/5-pyrimidinyl/thiocarbamates and process for preparing them |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS200101B1 (en) |
-
1977
- 1977-04-07 CS CS232677A patent/CS200101B1/en unknown
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