DE507525C - Process for the preparation of N-substituted benzimidazolonarsinic acids - Google Patents
Process for the preparation of N-substituted benzimidazolonarsinic acidsInfo
- Publication number
- DE507525C DE507525C DEI37091D DEI0037091D DE507525C DE 507525 C DE507525 C DE 507525C DE I37091 D DEI37091 D DE I37091D DE I0037091 D DEI0037091 D DE I0037091D DE 507525 C DE507525 C DE 507525C
- Authority
- DE
- Germany
- Prior art keywords
- acids
- substituted
- benzimidazolonarsinic
- preparation
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims description 14
- 150000007513 acids Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 chloroformic acid ester Chemical class 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 1
- CRXVBLLLPNWFBS-UHFFFAOYSA-N 4-aminobenzimidazol-2-one Chemical class NC1=CC=CC2=NC(=O)N=C12 CRXVBLLLPNWFBS-UHFFFAOYSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 150000008641 benzimidazolones Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/80—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von N-substituierten Benzimidazolonarsinsäuren In der Patentschrift 446 545 ist ein Verfahren zur Darstellung von N-substituierten Benzimidazolonarsinsäuren beschrieben, darin bestehend, daß Alkylamino-o-amino- oder Alkenylamino - o - aminobenzolarsinsäuren mit Phosgen behandelt werden. Gemäß Patent 489 459 kommt man zu denselben Verbindungen, wenn man Aminobenzimidazolone, die an dem einen Ringstickstoffatom durch Alkyl- oder Alkenylgruppen substituiert sind, dianotiert und die Diazoverbindungen mit arseniger Säure umsetzt. Es wurde nun gefunden, daß man diese wertvollen N-substituierten Benzimidazolonarsinsäuren auch erhalten kann, wenn Alkylamino-o-amino- oder Alkenylamino-oaminobenzolarsinsäuren mit Chlorameisensäureester umgesetzt und darauf mit Säuren behandelt werden. Unter Alkoholabspaltung gehen hierbei die primär gebildeten Carbäthoxyaminoderivate in Benzimidazolone über entsprechend folgendem Reaktionsschema NH # CH3 N , CH3 H,C . N 22 NH CO N#IHOC2H5 @# 3NH 2 @ @ H --> 1 4 i I I AsO,H2 AsOjH, As03H2 Beispiele i. 24,6 g 3-Ainino-4-methylaminobenzolr-arsinsäure werden in 125 ccm Wasser und 8,8 ccm Natronlauge von 40" B6 gelöst. Die Lösung wird auf o° abgekühlt. Unter Rüh. ren läßt man dann bei o bis 5° 13 g Chlorameisensäureäthylester und i o ccm Natronlauge von 4o° Be, die mit 15 ccm Wasser versetzt sind, gleichzeitig zutropfen, rührt, nachdem alles zugegeben -ist, noch etwa 3o Minuten nach und kocht nach Zugabe von 3o ccm konzentrierter Salzsäure auf. Nach kurzer Zeit beginnt die i-Methyl-2-oxobenzimidazol-2, 3-dihydrid-5-arsinsäure sich abzuscheiden. Sie wird abgesaugt und durch Umlösen aus Natronlauge oder Umkristallisieren aus Wasser gereinigt.Process for the preparation of N-substituted benzimidazolonarsinic acids In the patent specification 446 545 a process for the preparation of N-substituted benzimidazolonarsinic acids is described, which consists in treating alkylamino-o-amino- or alkenylamino-o-aminobenzolaric acids with phosgene. According to patent 489 459, the same compounds are obtained if aminobenzimidazolones, which are substituted on one ring nitrogen atom by alkyl or alkenyl groups, are dianotized and the diazo compounds are reacted with arsenic acid. It has now been found that these valuable N-substituted benzimidazolonarsinic acids can also be obtained if alkylamino-o-amino or alkenylamino-oaminobenzolar acids are reacted with chloroformic acid ester and then treated with acids. With elimination of alcohol, the carbethoxyamino derivatives primarily formed are converted into benzimidazolones via the following reaction scheme NH # CH3 N, CH3 H, C. N 22 NH CO N # IHOC2H5 @ # 3NH 2 @ @ H -> 1 4 i II AsO, H2 AsOjH, As03H2 Examples i. 24.6 g of 3-amino-4-methylaminobenzene arsic acid are dissolved in 125 cc of water and 8.8 cc of 40 "B6 sodium hydroxide solution. The solution is cooled to 0 °. The mixture is then left at 0 to 5 ° while stirring 13 g of ethyl chloroformate and sodium hydroxide solution of 4o cc io ° be, which are mixed with 1 5 cc of water, are added dropwise at the same time, stirring after all -is added, still about 3o minutes after cooking and after addition of 3o cc of concentrated hydrochloric acid. after a short After a while, the i-methyl-2-oxobenzimidazole-2,3-dihydride-5-arsinic acid begins to separate out. It is filtered off with suction and purified by dissolving it from sodium hydroxide solution or recrystallising it from water.
2. Die entsprechende i-Propyl-2-oxobenzimidazol-2, 3-dihydrid-5-arsinsäure erhält man durch Umsetzung von 27,4g 4-Propylamino-3-aminobenzol-i-arsinsäure mit Chlorameisensäureäthylester nach den in Beispiel i gemachten Angaben. 3. Werden 27,2 g 3-Amino-4-allylaminobenzol-i-arsinsäure mit i3 g Chlorameisensäureäthylester, wie in Beispiel i beschrieben, umgesetzt, so erhält man die i-Allyl-2-oxobenzimidazol-2, 3-dihydrid-5-arsinsäure.2. The corresponding i-propyl-2-oxobenzimidazole-2,3-dihydride-5-arsic acid is obtained by reacting 27.4 g of 4-propylamino-3-aminobenzene-i-arsic acid with Ethyl chloroformate according to the information given in Example i. 3. Be 27.2 g of 3-amino-4-allylaminobenzene-i-arsic acid with 13 g of ethyl chloroformate, as described in Example i, implemented, the i-allyl-2-oxobenzimidazole-2 is obtained, 3-dihydride-5-arsic acid.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI37091D DE507525C (en) | 1925-08-01 | 1929-02-12 | Process for the preparation of N-substituted benzimidazolonarsinic acids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF59486D DE446545C (en) | 1925-08-01 | 1925-08-01 | Process for the preparation of N-substituted benzimidazolonarsinic acids |
| DEI37091D DE507525C (en) | 1925-08-01 | 1929-02-12 | Process for the preparation of N-substituted benzimidazolonarsinic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE507525C true DE507525C (en) | 1930-09-18 |
Family
ID=25977707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI37091D Expired DE507525C (en) | 1925-08-01 | 1929-02-12 | Process for the preparation of N-substituted benzimidazolonarsinic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE507525C (en) |
-
1929
- 1929-02-12 DE DEI37091D patent/DE507525C/en not_active Expired
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