DE1545606A1 - Process for the preparation of new 5-nitrofuran derivatives - Google Patents
Process for the preparation of new 5-nitrofuran derivativesInfo
- Publication number
- DE1545606A1 DE1545606A1 DE19651545606 DE1545606A DE1545606A1 DE 1545606 A1 DE1545606 A1 DE 1545606A1 DE 19651545606 DE19651545606 DE 19651545606 DE 1545606 A DE1545606 A DE 1545606A DE 1545606 A1 DE1545606 A1 DE 1545606A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- compounds
- new
- germistatic
- nitrofuran
- 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.)
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung neuer 5-Nitrofuran-Derivate 5-Nitrofuran-Derivate der allgemeinen Formel in welcher die Substituenten Ri. und R2 Wasserstoff bedeuten oder gemeinsam zu einem Benzolring verknüpft sind, der gegebenenfalls eine Acylamino-oder Carboxygruppe tragen kann, sind bislang in der Literatur nicht beschrieben.Process for the preparation of new 5-nitrofuran derivatives 5-nitrofuran derivatives of the general formula in which the substituents R 1 and R 2 denote hydrogen or are linked together to form a benzene ring, which may optionally carry an acylamino or carboxy group, have not yet been described in the literature.
Es wurde gefunden, daß diese Verbindungen hervorragende germistatische Eigenschaften aufweisen. Im Vergleich zu bekannten Nitrofuran-Derivaten ergibt sich insbesondere eine verbesserte Wirksamkeit gegenüber Staphylococcus aureus, Escherichia coli und Streptococcus aureus sowie auch gegenüber Pilzen.These compounds have been found to be excellent germistatic Have properties. In comparison to known nitrofuran derivatives results in particular an improved effectiveness against Staphylococcus aureus, Escherichia coli and Streptococcus aureus as well as against fungi.
Das erfindungsgemäße Verfahren zur Herstellung der neuen 5-Nitrofuran-Derivate ist dadurch gekennzeichnet, dal3 man 5-Nitrofurfurel bzw. dessen Diacetat mit Verbindungen der allgemeinen Formel in welcher R1 und R2 die oben angegebene Bedeutung haben, kondensiert, wobei man gegebenenfalls den Substituenten des Benzolrings auch erst nach erfolgter Kondensation durch Verseifung einführt bzw. freisetzt.The process according to the invention for the preparation of the new 5-nitrofuran derivatives is characterized in that 5-nitrofurfurel or its diacetate is mixed with compounds of the general formula in which R1 and R2 have the meaning given above, condensed, the substituents of the benzene ring optionally also being introduced or released by saponification only after the condensation has taken place.
B-e i s p i e 1 e 1.) 1-t5-Nitro-2-furyl)-2-(2-benzthiazolyl)-äth. ylen 2,82 g 2-Methyl-benzthiazol werden mit 2, 82 g 5-Nitro-2-fural und 4 g Acetanhydrid 2 Stunden auf 130° (Badtemperatur) erhitzt ; nach dem Erkalten wird mit Wasser versetzt, mit Natriumbicarbonat neutralisiert, abgesaugt und der Niederschlag mit Wasser gewaschen. Man kocht nun 4mal mit Benzol aus (jeweils mit 80 ml, 60 ml, 40 ml bzw. 20 ml) und dampft die klare Benzolloesung im Vakuum ein. Der Rückstand liefert nach Umkristallisation aus 20 ml Dioxan 1, 75 g 1- (5-Nitro-2-furyl)-2- (2-benzthiazolyl)-äthylen vom Fp. 202-204° (Zers.) 2.) 1-(5-Nitro-2-furyl)-2-(2-thiazolYl)-äthylen 1,5 g 2-Methyl-thiazol, 3 g Acetanhydrid, 0, 9 g Eisessig und 2, 1 g 5-Nitro-2-fural erhitzt man 2 Stunden auf 160°, saugt nach Erkalten das ausgeschiedene Produkt ab und wascht mit Eisessig nach (1, 5 g). Man loest die Substanz in heißem Benzol, trennt von ungeloestem Material ab und dampft im Vakuum zur Trockene ein. Auf diese Weise erhält man 1,25 g 1- (5-Nitro-2-furyl)-2-(2-thiazolyl)-äthylen vom Fp. 154-156° (aus Acetonitril). B-e i s p i e 1 e 1.) 1-t5-nitro-2-furyl) -2- (2-benzthiazolyl) eth. ylen 2.82 g of 2-methylbenzothiazole are mixed with 2.82 g of 5-nitro-2-fural and 4 g of acetic anhydride Heated to 130 ° (bath temperature) for 2 hours; after cooling, water is added, neutralized with sodium bicarbonate, filtered off with suction and the precipitate washed with water. It is now boiled 4 times with benzene (each with 80 ml, 60 ml, 40 ml or 20 ml) and the clear benzol solution evaporates in a vacuum. The residue yields after recrystallization from 20 ml of dioxane 1.75 g of 1- (5-nitro-2-furyl) -2- (2-benzthiazolyl) ethylene of melting point. 202-204 ° (decomp.) 2.) 1- (5-Nitro-2-furyl) -2- (2-thiazolYl) ethylene 1.5 g of 2-methyl-thiazole, 3 g of acetic anhydride, 0.9 g of glacial acetic acid and 2.1 g of 5-nitro-2-fural are heated for 2 hours to 160 °, sucks off the precipitated product after cooling and washed with glacial acetic acid according to (1.5 g). The substance is dissolved in hot benzene and separated from undissolved material and evaporated to dryness in a vacuum. In this way, 1.25 g of 1- (5-nitro-2-furyl) -2- (2-thiazolyl) ethylene are obtained of m.p. 154-156 ° (from acetonitrile).
C9H6N203S (222) Ber. N 12,61 % ; S 14, 43 % ; Gef. N 12, 68 % ; S 14, 4%. C9H6N203S (222) Calc. N 12.61%; S 14, 43%; Found N 12, 68%; S. 14.4%.
3.) 1- 5-Nitro-2-furyl)-2- (6-acetamido-2-benzthiazolyl)-athylen @ g 2-Methyl-6-amino-benzthiazol (Fp. 123-124°) wird mit 3 ml Acetanhydrid 15 Min. auf 160° (Badtemperatur) unter RUckfluB erhitzt, dann mit 0, 86 g 5-Nitro-2-furfural versetzt und 2 Stdn. auf derselben Temperatur gehalten. Nach Stehen über Nacht bei Raumtemperatur saugt man das ausgeschiedene Material ab, wäscht mit Eisessig nach, kristallisiert den FilterrUckstand (1, 3 g) aus 4 ml Dimethylformamid um, wobei 0, 5 g Kristalle vom Fp. 258-266° (Zers.) erhalten werden.3.) 1- 5-Nitro-2-furyl) -2- (6-acetamido-2-benzthiazolyl) -ethylene @ g of 2-methyl-6-aminobenzothiazole (melting point 123-124 °) is mixed with 3 ml of acetic anhydride for 15 min. heated to 160 ° (bath temperature) under reflux, then with 0.86 g of 5-nitro-2-furfural offset and Maintained at the same temperature for 2 hours. After standing The precipitated material is filtered off with suction at room temperature overnight and washed with After glacial acetic acid, the filter residue (1.3 g) crystallizes from 4 ml of dimethylformamide to, whereby 0.5 g of crystals with a melting point of 258-266 ° (dec.) are obtained.
C15H11N3O4S (329) Ber. C 54,7 % ; H 3,34 %; N 12,77 % S 9,72 %; Gef. C 54,68 %; H 3,55 %; N 12,55 %; S 9,8 %. C15H11N3O4S (329) Calc. C 54.7%; H 3.34%; N 12.77% S 9.72%; Found C 54.68%; H 3.55%; N 12.55%; S 9.8%.
Die orangefarbenen Kristalle werden beim Erhitzen auf etwa 100° rot. Aus der mit Wasser gefällten Dimethylformamid-Mutterlauge koennen noch weitere Mengen dieser Substanz erhalten werden. The orange crystals turn red when heated to about 100 °. Further amounts can be obtained from the dimethylformamide mother liquor precipitated with water this substance can be obtained.
4.) 1-(5-Nitro-2-£uryl)-2-(6-carboxy-2-benzthiazoly äthylen 1. 1 g 2-Methyl-6-carbäthoxy-benzthiazol loest man in 2, 5 S Acetanhydrid und 0, 6 g Eisessig, gibt 0, 8 g 5-Nitro-2-furfural zu und erhitzt 3 Stdn. auf 160° Badtemperatur unter RUckfluB. Nach dem Erkalten wird abgesaugt, mit Eisessig gewaschen und aus 8 ml Dioxan umkristallisiert. Ausbeute : 1, 1 g ; Fp. 179-181°.4.) 1- (5-Nitro-2-uryl) -2- (6-carboxy-2-benzthiazolyethylene 1.1 g 2-Methyl-6-carbethoxy-benzothiazole is dissolved in 2.5 S acetic anhydride and 0.6 g of glacial acetic acid, is 0.8 g of 5-nitro-2-furfural and heated for 3 hours. To 160 ° bath temperature below Return flow. After cooling, it is suctioned off, washed with glacial acetic acid and 8 ml Dioxane recrystallized. Yield: 1.1 g; 179-181 °.
C16H12N2O5S (344) Ber. C 55,8 %; N 3,49 %; N 8,14 %; S 9,3 %; Gef. C 55. 56 % ; N 3. 66 % ; N 7, 88 % ; S 9, 5 %. C16H12N2O5S (344) Calc. C 55.8%; N 3.49%; N 8.14%; S 9.3%; Found C 55.56%; N 3. 66%; N 7.88%; S 9.5%.
1 g dieses Esters wird in 15 ml 90 % iger, wässriger heiBer Ameisensäure geloest, mit 4. 4 g Methansulfonsäure versetzt und-2 Stnd. am RUckfluB auf 110° Badtemperatur erhitzt. Dann wird im Vakuum auf das halbe Volumen eingedampft und mit der ca. 20-fachen Menge Wasser versetzt ; das dabei ausgeschiedene Material wird abgesaugt (1,05 g) und noch feucht aus Dioxan n umkristallisiert. 1 g of this ester is dissolved in 15 ml of 90% aqueous hot formic acid dissolved, mixed with 4. 4 g of methanesulfonic acid and -2 hours. at the return flow to 110 ° Heated bath temperature. It is then evaporated to half its volume in vacuo and mixed with approx. 20 times the amount of water; that which was eliminated material is suctioned off (1.05 g) and recrystallized from dioxane n while still moist.
Ausbeute : 0,5 g ; Fp. 286-288° (Zers., ab 278° Verfärbung).Yield: 0.5 g; Mp. 286-288 ° (decomp., Discoloration from 278 °).
C14H8N205S (316) Ber. C 53, 2 % ; H 2, 53 % ; N 8,86 % ; S 10, 13 % ; Gef. C 53.25%;H2,85%;N8,52%;S9.8%.C14H8N205S (316) Ber. C 53.2%; H 2, 53%; N 8.86%; S 10, 13 %; Found C 53.25%; H2.85%; N8.52%; S9.8%.
Die so erhaltene Säure gibt ein in Wasser schwer loesliches Natriumsalz ; das entsprechende Ammoniumsalz ist in Wasser leichter loeslich.The acid obtained in this way gives a sodium salt which is sparingly soluble in water ; the corresponding ammonium salt is more easily soluble in water.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB0083024 | 1965-07-29 |
Publications (1)
Publication Number | Publication Date |
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DE1545606A1 true DE1545606A1 (en) | 1969-08-07 |
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ID=6981768
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DE19651545606 Pending DE1545606A1 (en) | 1965-07-29 | 1965-07-29 | Process for the preparation of new 5-nitrofuran derivatives |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2920247A1 (en) * | 1978-05-19 | 1979-11-22 | Kureha Chemical Ind Co Ltd | ANTITUMOR AGENTS |
-
1965
- 1965-07-29 DE DE19651545606 patent/DE1545606A1/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2920247A1 (en) * | 1978-05-19 | 1979-11-22 | Kureha Chemical Ind Co Ltd | ANTITUMOR AGENTS |
DE2920247C2 (en) * | 1978-05-19 | 1985-09-19 | Kureha Kagaku Kogyo K.K., Tokio/Tokyo | Use of a nitrofuryl-vinylene-thiazole-N-oxide compound for the preparation of anti-tumor agents |
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