CS232338B1 - Processing of alkylester 5-(5-phenyl-2-furyl)tetrasol-2-acetic acid - Google Patents
Processing of alkylester 5-(5-phenyl-2-furyl)tetrasol-2-acetic acid Download PDFInfo
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- CS232338B1 CS232338B1 CS833943A CS394383A CS232338B1 CS 232338 B1 CS232338 B1 CS 232338B1 CS 833943 A CS833943 A CS 833943A CS 394383 A CS394383 A CS 394383A CS 232338 B1 CS232338 B1 CS 232338B1
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- Czechoslovakia
- Prior art keywords
- furyl
- phenyl
- tetrazol
- ethyl
- formula
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- 125000005907 alkyl ester group Chemical group 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- -1 5- [5- (4-Chloro-phenyl) -2-furyl] -tetrazol-2-yl-ethyl-ethyl Chemical group 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- ARBBMMZDMWCLNA-UHFFFAOYSA-N 5-(5-phenylfuran-2-yl)-2H-tetrazole Chemical class C=1C=C(C=2C=CC=CC=2)OC=1C=1N=NNN=1 ARBBMMZDMWCLNA-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- YCFQFIJEDGUUMG-UHFFFAOYSA-N OC(=O)CN1N=NC(C=2OC(=CC=2)C=2C=CC=CC=2)=N1 Chemical class OC(=O)CN1N=NC(C=2OC(=CC=2)C=2C=CC=CC=2)=N1 YCFQFIJEDGUUMG-UHFFFAOYSA-N 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 102100026450 POU domain, class 3, transcription factor 4 Human genes 0.000 description 1
- 101710133389 POU domain, class 3, transcription factor 4 Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Description
Vynález sa týká alkylesterov 5-[5-fenyl-2-furyl^tetrazol-2-yloctových kyselin všeobecného vzorca I (i), v ktorom Alk představuje metyl, etyl, n-propyl a R představuje vodík, bróm, chlór, metyl, metoxy a nitro-skupinu v polohe o-, m-, alebo p-fenylového jadra a spšsob ich přípravy.The invention relates to alkyl esters of 5- [5-phenyl-2-furyl-4-tetrazol-2-ylacetic acids of formula I (i) wherein Alk is methyl, ethyl, n-propyl and R is hydrogen, bromo, chloro, methyl, a methoxy and nitro group in the o-, m-, or p-phenyl position and a process for their preparation.
Tieto nové v literatúre nepopísané zlúčeniny sa používajú ako medziprodukty v syntézách áalších biologicky účinných látok.These novel compounds not described in the literature are used as intermediates in the synthesis of other biologically active substances.
Látky podl’a vynálezu sa pripravujú reakciou 5[5-fenyl-2-furyl]tetrazolov všeobecného vzorca II (II), v ktorom R má ten istý význam ako vo vzorci I, alebo ich anorganických, resp. organických solí s halogenoctanom alkylovým všeobecného vzorca IIIThe compounds according to the invention are prepared by reacting 5 [5-phenyl-2-furyl] tetrazoles of the general formula II (II), in which R has the same meaning as in the formula I, or their inorganic, resp. organic salts of alkyl haloacetate of formula III
X-CH2-CO2Alk (III), v ktorom X je chlór, bróm, jód a Alk má ten istý význam ako vo vzorci I. Reakciou vzniká aj izomér s karbalkoxymetylovou skupinou v polohe 1 tetrazolového kruhu.X-CH 2 -CO 2 Alk (III) in which X is chlorine, bromine, iodine and Alk has the same meaning as in Formula I. The reaction also produces an isomer with a carbalkoxymethyl group at the 1-position of the tetrazole ring.
Postup přípravy zlúčenin podl’a vynálezu sa uskutočňuje tak, že sa z 5-^5-fenyl-2-furylJtetrazolov vzorca II připraví sodná, alebo draselné sol’ ich zaiešaním s alkoholétom sodným, alebo draselným v alkohole s počtom uhlikov 1 až 3, s výhodou v etanole. K roztoku vzniklej sodnéj, alebo draselnej soli v alkohole sa přidá alkylester halogenootovej kyseliny vzorca III, s výhodou brómoctan a zmes sa zahrieva při 40 °C až 100 °C, s výhodou pri 50 °C až 80 °C v priebehu 2 až 20 h.The process for the preparation of the compounds according to the invention is carried out by preparing the sodium or potassium salt of 5- (5-phenyl-2-furyl) tetrazoles of formula II by mixing them with sodium or potassium alcohol in an alcohol having a carbon number of 1 to 3, preferably in ethanol. To a solution of the formed sodium or potassium salt in an alcohol is added an alkyl ester of a halenoic acid of formula III, preferably bromoacetate, and the mixture is heated at 40 ° C to 100 ° C, preferably at 50 ° C to 80 ° C for 2 to 20 h .
Namiesto samotných alkoholov s počtom uhlikov 1 až 3 je možné použiť ako reakčné prostredie ich zmesi s vodou, alebo ketony, napr. aceton, metylétylketón.Instead of the alcohols having a carbon number of 1 to 3 alone, mixtures thereof with water or ketones, e.g. acetone, methyl ethyl ketone.
Chladením reakčnej zmesi vykrystalizuje zmes polohových izomérnych esterov, z ktorých sa vedTajši produkt oddělí od látky vzorca I chromatogreficky.By cooling the reaction mixture, a mixture of positional isomeric esters crystallizes, from which the by-product is separated from the compound of formula I by chromatography.
V ňalšom je prevedenie vynálezu popísané v príkladooh bez toho, že by sa na tieto obmezoval.In the following, an embodiment of the invention is described by way of example without being limited thereto.
Příklad 1Example 1
5-[5-(4-chlórfenyl)-2-furyl]tetrazol-2-yloc tan etylový5- [5- (4-Chloro-phenyl) -2-furyl] -tetrazol-2-ylocyl-ethyl
V suchom etanole (350 ml) sa rozpustí sodík (2,3 g, 0,1 mol), a potom 5-[5-(4-chlórfenyl)-2-furyl]-1H-1-tetrazol (24,66 g, 0,1 mol). Roztok sa zohreje do varu etanolu a po 5 min sa přidá brómoctan etylový (11,13 ml, 0,1 mol). Reakčná zmes sa zahrieva pri vare etanolu 16 h, potom sa ochladí, vykrystalizovaná zmes esterov odfiltruje a premyje etanolom. Po vysušení sa polohové izoméry rozdelia chromatogreficky. Výťažok 37,5%. T.t. 99-101 °C (etanol). Pře C^Hj^ClN^Q^ vypočítané, resp. nájdené: 54,14 resp. 54,38 % C, 3,93 resp.Sodium (2.3 g, 0.1 mol) was dissolved in dry ethanol (350 mL) followed by 5- [5- (4-chlorophenyl) -2-furyl] -1H-1-tetrazole (24.66 g). , 0.1 mol). Heat the solution to boiling ethanol and add ethyl bromoacetate (11.13 mL, 0.1 mol) after 5 min. The reaction mixture is heated under boiling ethanol for 16 h, then cooled, the crystallized ester mixture is filtered off and washed with ethanol. After drying, the positional isomers are separated by chromatography. Yield 37.5%. MP: 99-101 ° C (ethanol). For C ^ HHj ^ClN ^ Q ^ ^ calculated, respectively. found: 54.14 resp. C, 54.38;
3,84 % H, 16,83 resp. 16,93 % N a 10,64 resp. 10,72 % Cl.% H, 3.84; 16.93% N and 10.64 resp. 10.72% Cl.
Příklad 2Example 2
5- [5-.( 3-ehlórfenyl) -2-furyl]tetrazol-2-yloctan etylový5- [5- (3-chlorophenyl) -2-furyl] tetrazol-2-yl-ethyl acetate
Bol připravený analogickým postupom ako v příklade 1. z 5-[5-(3-chlórfenyl)-2-furyl]-1H-1-tetrazolu (24,66 g, 0,1 mol). Výťažok 40,9«. T.t. 126-127 (etanol). Pre vypočítané, resp. nájdené: 54,14 resp. 54,42 « C, 3,93 resp. 3,81 « H, 16,83 resp. 16,93 % N a 10,65 resp. 10,69 «Cl.Prepared in analogy to Example 1. from 5- [5- (3-chlorophenyl) -2-furyl] -1H-1-tetrazole (24.66 g, 0.1 mol). Yield 40.9%. MP: 126-127 (ethanol). For calculated, respectively. found: 54.14 resp. 54.42 ° C, 3.93 resp. 3.81 " H, 16.83 resp. 16.93% N and 10.65 resp. 10.69 «Cl.
Příklad 3Example 3
5-[5-chlórfenyl)-2-furyl]tetrazol-2-yloctan etylový5- [5-Chloro-phenyl) -2-furyl] -tetrazol-2-yl-ethyl acetate
Bol připravený analogickým postupom ako v příklade 1. z 5-[5-(2-chlórfenyl)-2-furylj-1H-1-tetrazolu (24,66 g, 0,1 mol). Výťažok 41,8«. T.t. 88-89 °C (etanol). Pre C^H^CIN^ vypočítané, resp. nájdené: 54,14 resp. 54,24 « C, 3,93 resp. 3,91 « H, 16,83 resp. 16,99 « N a 10,65 resp. 10,88 « Cl.Prepared in analogy to Example 1 from 5- [5- (2-chloro-phenyl) -2-furyl] -1 H-1-tetrazole (24.66 g, 0.1 mol). Yield 41.8%. MP: 88-89 DEG C. (ethanol). For C? H? CIN? found: 54.14 resp. 54.24 ° C, 3.93 resp. 3.91 < H > 16.99 «N and 10.65 resp. 10.88 «Cl.
Příklad 4Example 4
5-[5-(4-brómfenyl)-2-furyl]tetrazol-2-yloctan etylový5- [5- (4-Bromo-phenyl) -2-furyl] -tetrazol-2-yl-ethyl-ethyl
Bol připravený analogickým postupom ako v příklade 1. z 5-[5-(4-brómfenyl)-2-furyl]- 1H-1-tetrazolu (29,11 g, 0,1 mol). Výťažok 38,6«. T.t. 105-106 °C (etanol). Pre CjjH^BrN^O^ vypočítané resp. nájdené: 47,76 resp. 47,91 « C, 3,47 resp. 3,50 « H, 14,85 resp. 14,55 «Na 21,18 resp. 21,84 « Br.Prepared in analogy to Example 1 from 5- [5- (4-bromophenyl) -2-furyl] -1H-1-tetrazole (29.11 g, 0.1 mol). Yield 38.6%. MP: 105-106 ° C (ethanol). For C 11 H 14 BrN 4 O 4 calculated or calcd. found: 47.76 resp. 47.91 ° C, 3.47 resp. 3.50 ' 14.55 «At 21.18 resp. 21.84 «Br.
Příklad 5Example 5
5-[5-(3-metylfenyl)-2-furyl]tetrazol-2-yloctan etylový5- [5- (3-Methylphenyl) -2-furyl] tetrazol-2-yl-ethyl acetate
Bol připravený analogickým postupom ako v příklade 1. z 5-[5-(3-metylfenyl)-2-furyl]-1H-1-tetrazolu (22,62 g, 0,1 mol). Výťažok 32,2«. T.t. 96-97 °C (eťanol). Pře C^gH^gN^O^ vypočítané, resp. nájdené: 61,53 resp. 61,49 « C, 5,16 resp. 5,20 « H, 17,90 resp.Prepared in analogy to Example 1. from 5- [5- (3-methylphenyl) -2-furyl] -1H-1-tetrazole (22.62 g, 0.1 mol). Yield 32.2%. MP: 96-97 ° C (ethanol). For C ^ ^HH gNNO ^ calculated, respectively. found: 61.53 resp. 61.49 ° C, 5.16 resp. 5.20, H, 17.90 and 3.20, respectively.
17,94 » N.17,94 »N.
Příklad 6Example 6
5-[5-(4-metoxyfenyl)-2-fmryl]tetrazol-2-yloctan etylový5- [5- (4-Methoxyphenyl) -2-formyl] tetrazol-2-yl-ethyl acetate
Bol připravený analogickým postupom ako v příklade 1. z 5-[5-(4-metoxyfenyl)-2-furylj-1H-1-tetrazolu (24,22 g, 0,1 mol). Výťažok 37,9«. T.t. 90-92 °C (etanol). Pre CjgH^O* vypočítané, resp. nájdené: 58,53 resp. 58,20 « C, 4,91 resp. 5,05 «Ha 17,06 resp. 17,10 « N.Prepared in a manner analogous to Example 1, starting from 5- [5- (4-methoxyphenyl) -2-furyl] -1H-1-tetrazole (24.22 g, 0.1 mol). Yield 37.9%. MP: 90-92 ° C (ethanol). For C 18 H 16 O 3 calculated, respectively. found: 58.53 resp. 58.20 ° C, 4.91 resp. 5.05 «Ha 17.06 resp. 17,10 «N.
Příklad 7 ' 5-[5-metoxyfenyl)-2-furyl]tetrazol-2-yloctan etylovýExample 7 '5- [5-Methoxy-phenyl) -2-furyl] -tetrazol-2-yl-ethyl-ethyl
Bol připravený analogickým postupom ako v příklade 1. z 5-[.5-(2-metoxyfenyl)-2-furyl]-1H-1-tetrazolu (24,22 g, 0,1 mol)., s tým rozdielom, že alkylácia sa robila s cblóroctanom stylovým (12,25 g, 0,1 mol). Výťažok 39,5«. T.t. 109-110 eC (etanol). Pre C^HjgM^ vypočítané, resp. nájdené: 58,53 resp. 58,50 « C, 4,91 resp. 4,98 «Ha 17,06 resp. 17,10 « N.Prepared in analogy to Example 1 from 5- [5- (2-methoxyphenyl) -2-furyl] -1H-1-tetrazole (24.22 g, 0.1 mol), except that alkylation was carried out with stylish chloroacetate (12.25 g, 0.1 mol). Yield 39.5%. Mp 109-110 e C (ethanol). For C, HHggM ^ calculated, respectively. found: 58.53 resp. 58.50 < C > 4.98 «Ha 17.06 resp. 17,10 «N.
Příklad .8Example .8
5-[5-(2-nitrofenyl)-2-furyl]tetrazol-2-yloctan etylový5- [5- (2-Nitrophenyl) -2-furyl] tetrazol-2-yl-ethyl acetate
V suchom metanole (350 ml) sa rozpustí draslík (3,91 g, 0,1 mol), a potom 5-(5-(2-nitrofenyl)-2-furyl]-1H-1-tetrazol (25,72 g, 0,1 mol). Roztok sa zahřeje do varu metanolu a po 5 min sa přidá brómoctan etylový (11,13 ml, 0,1 mol). Reakčná zmes sa zahrieva pri vare metanolu 20 h, a potom sa spraeuje ako v příklade 1. Výťažok 52%. T.t. 100-101 °C (etanol). Pre C^H^N^O^ vypočítané, resp. nájdené: 52,48 resp. 52,25 % C, 3,81 resp.Potassium (3.91 g, 0.1 mol) was dissolved in dry methanol (350 mL) followed by 5- (5- (2-nitrophenyl) -2-furyl) -1H-1-tetrazole (25.72 g). The solution is heated to the boiling of methanol and after 5 min ethyl bromoacetate (11.13 ml, 0.1 mol) is added and the reaction mixture is heated at boiling methanol for 20 h and then treated as in the example. 1. Yield 52%, mp 100-101 ° C (ethanol) For C) HH C NN ^O ^, calculated and found: C, 52.48 and 52.25%, C, 3.81, respectively.
3,90 % H a 20,40 resp. 20,68 % N.3.90% H and 20.40 resp. 20.68% N.
Příklad 9Example 9
5-[5-(fenyl)-2-furyl]tetrazol-2-yloctan etylový5- [5- (phenyl) -2-furyl] tetrazol-2-yl-ethyl acetate
Bol připravený analogickým postupom ako v příklade 8. z 5-[5-(fenyl)-2-furyl]-1H-1-tetrazolu (21,22 g, 0,1 mol). Výťažok 39,2%. T.t. 84-86 °C (etanol). Pre vypočítané, resp. nájdené: 60,39 resp. 60,42 % C, 4,73 resp. 4,50 % a 18,78 resp. 18,64 % NPrepared in analogy to Example 8 from 5- [5- (phenyl) -2-furyl] -1H-1-tetrazole (21.22 g, 0.1 mol). Yield 39.2%. MP: Mp 84-86 ° C (ethanol). For calculated, respectively. found: 60.39 resp. % C, 60.42; 4.73; 4.50% and 18.78, respectively. N, 18.64
Claims (12)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS833943A CS232338B1 (en) | 1983-06-01 | 1983-06-01 | Processing of alkylester 5-(5-phenyl-2-furyl)tetrasol-2-acetic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS833943A CS232338B1 (en) | 1983-06-01 | 1983-06-01 | Processing of alkylester 5-(5-phenyl-2-furyl)tetrasol-2-acetic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS394383A1 CS394383A1 (en) | 1984-06-18 |
| CS232338B1 true CS232338B1 (en) | 1985-01-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS833943A CS232338B1 (en) | 1983-06-01 | 1983-06-01 | Processing of alkylester 5-(5-phenyl-2-furyl)tetrasol-2-acetic acid |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS232338B1 (en) |
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1983
- 1983-06-01 CS CS833943A patent/CS232338B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS394383A1 (en) | 1984-06-18 |
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