PL14743B1 - The method obtained double-substituted tetrazoles. - Google Patents
The method obtained double-substituted tetrazoles. Download PDFInfo
- Publication number
- PL14743B1 PL14743B1 PL14743A PL1474330A PL14743B1 PL 14743 B1 PL14743 B1 PL 14743B1 PL 14743 A PL14743 A PL 14743A PL 1474330 A PL1474330 A PL 1474330A PL 14743 B1 PL14743 B1 PL 14743B1
- Authority
- PL
- Poland
- Prior art keywords
- substituted
- tetrazoles
- method obtained
- substituted tetrazoles
- obtained double
- Prior art date
Links
- 150000003536 tetrazoles Chemical class 0.000 title claims description 9
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
W patentach niemieckich NrNr 439041 i 455585 sa opisane sposoby, wedlug któ¬ rych mozna otrzymywac tetrazole z keto¬ nów i kwasu trójazotowodorowego. Sposo¬ by te okazaly sie szczególnie korzystnemi w celu otrzymania dwukrotnie podstawio¬ nych tetrazoli typu pieciometylenotetra- zolu.Stwierdzono obecnie, iz mozna takie same dwukrotnie podstawione tetrazole o- trzymac w ten sposób, iz imidochlorki, podstawione chlorowcem, przemienia sie zapomoca kwasu trójazotowodorowego lub azydów na tetrazole, podstawione chlo¬ rowcem, a nastepnie ze zwiazków tych u- suwa sie chlorowiec przez redukcje lub u- wodornienie.Przyklad. Do roztworu 22.6 g e-leu- cynolaktamu (0.2 czasteczki) w mniej wie¬ cej 50 om3 ksylblu, wprowadza sie, chlo¬ dzac, 125 g pieciochloiiku fosforu (0.6 cza¬ steczki) i ogrzewa na lazni olejowej przy 1400|C az do wytworzenia klarownego roz¬ tworu. Po oddestylowaniu PC/3 (trójchlor¬ ku fosforu), POCls (ttlenotrójchlorku fosfo¬ ru) i ksylolu w prózna, pozostaje imido- chlorek dwuchloroleufcynolaktamu (II) (J. v. Braun B. 63,506/1930) w postaci jasno- brunatnego plynu, który (bez dalszego oczy¬ szczania wprowadza sie, chlodzac równo¬ czesnie, do 100 ctm3 2,6 n-lbenzólowego roz¬ tworu kwasu trójazotowodorowego. Po krótkiem staniu (wydzielanie kwasu solne¬ go) odparowuje sie mieszanine mozliwiedo sucha. Pozostalosc, skladajaca sie z su¬ rowego dwuchlo*opentametylenotetrazolu (III) (pttott topnienia czystego produktu 870C) rozpuszcza sie w kwasie octowym lodowatym i ma goraco dodaje stopniowo 40 g pylku cynkowego. Rozcienczony woda roztwór odlewa sie od niezuzytego cynku, zadaje mocnym lugiem sodowym i wstrza¬ sa z benzolem. Po odparowaniu benzolu poddaje sie pozostalosc destylacji frakcjo¬ nowanej w prózni. Glownia frakcja sklada sie z piecio-metylenotetrazolu.I CH2-CH2-CO CHo ^CHz-CHt-NH III ,CHs-CCk-C-N.Cffa N ^CHs-CHs-N-N^ II CH2-CCk-C-Cl Cfl2- CH.-N CH»-CH*-C = N.CHo-CHi-N-N \ N y PLThe German Patent Nos. 439041 and 455585 describe methods by which tetrazoles can be obtained from ketones and trinohydric acid. These methods have proved to be particularly advantageous for the preparation of doubly substituted tetrazoles of the pentomethylene tetrazole type. It has now been found that the same doubly substituted tetrazoles can be made in such a way that the halogen-substituted imidochlorides are converted with trihydric acid or azides to tetrazoles, substituted with halogen, and then from these compounds the halogen is removed by reduction or hydrogenation. Example. To a solution of 22.6 g of e-leucinolactam (0.2 molecules) in approximately 50 µm3 of xylbl, 125 g of phosphorus pentachloride (0.6 molecules) are added under cooling and heated in an oil bath at 1400 µC until preparation of a clear solution. After distilling PC / 3 (phosphorus trichloride), POCl (phosphorus trichloride) and xylol in vacuum, the remains of dichloroleufcinolactam (II) imido chloride (J. v. Braun B. 63, 506/1930) as a light brown liquid which (without further purification) is introduced while cooling to 100 cc of a 2.6 N-benzoic trinohydric acid solution. After a short standing (evolution of hydrochloric acid), the mixture is evaporated as dry as possible. from crude di-opentamethylene tetrazole (III) (the melting point of pure product 870C) is dissolved in glacial acetic acid and 40 g of zinc pollen are added hotter. The diluted water solution is poured from unused zinc, added with strong sodium hydroxide and shaken. are with benzol. After the benzol has been evaporated, the residue is subjected to fractional distillation in a vacuum. The main fraction consists of pentamethylenetetrazole.I CH2-CH2-CO CHo ^ CHz-CHt-NH III, CHs-CCk-CN.Cffa N ^ CHs-CHs-NN ^ II CH2- CCk-C-Cl Cfl2- CH.-N CH »-CH * -C = N.CHo-CHi-N-N \ N y PL
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL14743B1 true PL14743B1 (en) | 1931-11-30 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL14743B1 (en) | The method obtained double-substituted tetrazoles. | |
| DE612870C (en) | Process for the preparation of dyes of the anthraquinone series | |
| DE700982C (en) | Process for the preparation of partially hydrogenated 7-alkoxy-1-ketophenanthrenes | |
| DE400969C (en) | Process for the production of thymol (1-methyl-4-isopropyl-3-oxybenzene) | |
| DE609997C (en) | Process for the preparation of primary phosphates of amino acid esters | |
| Rao et al. | Chemical examination of Erythrina indica | |
| DE490358C (en) | Process for the preparation of perinaphtindones | |
| DE704762C (en) | Process for the preparation of dihydrobenzoisoquinolines | |
| DE638601C (en) | Process for the preparation of anthraquinone dyes | |
| DE632136C (en) | Process for the production of acidic dyes of the anthraquinone series | |
| DE510433C (en) | Process for the preparation of porphyrins | |
| DE564435C (en) | Process for the preparation of Dihalogenanthraquinone mono-ª ‡ -carboxylic acids | |
| DE338735C (en) | Process for the preparation of complex iron compounds of phosphoric acid esters of higher aliphatic polyhydroxyl compounds | |
| DE488624C (en) | Process for the representation of dyes | |
| DE657724C (en) | Process for the nucleus alkylation of polyhydric phenols | |
| DE703776C (en) | Process for the production of clumps of 3, 5-diiodoxybenzene-1-carboxylic acids | |
| DE445847C (en) | Process for the preparation of cerulin sulfonic acids | |
| DE646300C (en) | Process for the preparation of 1- (N) -9-Anthrapyridonsulfonsäuren | |
| DE862452C (en) | Process for the preparation of 5-aminoisophthaloyl-bis-acetonitrile | |
| DE414260C (en) | Process for the preparation of halogenated oxythionaphthens | |
| DE493688C (en) | Process for the production of ketones of the anthracene series | |
| DE494597C (en) | Process for the preparation of anthracene thioglycolic acid and anthracene-2, 1-oxythiophene | |
| CH215287A (en) | Process for the preparation of a compound of the unsaturated cyclopentanopolyhydrophenanthrene series. | |
| CH131288A (en) | Process for the preparation of a polysulfide ester of an aromatic carboxylic acid. | |
| CH120442A (en) | Process for the preparation of a compound from isopropylpropenylbarbituric acid and 4-dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone. |