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CH438332A - Process for the synthesis of nitrofuran compound - Google Patents

Process for the synthesis of nitrofuran compound

Info

Publication number
CH438332A
CH438332A CH207561A CH207561A CH438332A CH 438332 A CH438332 A CH 438332A CH 207561 A CH207561 A CH 207561A CH 207561 A CH207561 A CH 207561A CH 438332 A CH438332 A CH 438332A
Authority
CH
Switzerland
Prior art keywords
process according
subclaim
base
synthesis
base used
Prior art date
Application number
CH207561A
Other languages
Italian (it)
Inventor
Concillio Carlo
Marangoni Luigi
Original Assignee
Zambon Spa
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Zambon Spa filed Critical Zambon Spa
Publication of CH438332A publication Critical patent/CH438332A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Procedimento per la sintesi di composte nitrofuranico La présente iuvenzione concerne un procedimento per la sintesi della 5-idrossimetil-l-(5'-nitro-furfurilide- nammino)-idantoina, di formula Process for the synthesis of nitrofuran compounds The present invention relates to a process for the synthesis of 5-hydroxymethyl-1-(5'-nitro-furfurylidenamino)-hydantoin, of the formula

intermedio nitrofuranico particolarmente adatto per et, tenere composti chemioterapici di tipo nitrofuranico, con- traddistinguentisi per 'la loro buona idrosolubilità e quin- di per i vantaggi che da talé proprietà discendono e de- scritti nel brevette Svizzero Nr. 435 299 a nome della stessa richiedente. nitrofuran intermediate particularly suitable for keeping chemotherapeutic compounds of the nitrofuran type, distinguished by their good water solubility and therefore by the advantages that derive from this property and described in the Swiss patent No. 435 299 in the name of the same applicant.

Il procxdimento per la preparazione del nuovo com- poste nitrofuranico si caratterizza per il fatto che la 1-(5'-@nitro-furfurilidenamino)- idantoina di formula The process for the preparation of the new nitrofuric compound is characterized by the fact that the 1-(5'-@nitro-furfurylidenamino)- hydantoin of formula

viene condensata con aldeide formica. ESEMPIO 1 Preparazione della 5-Idrossimetil-l-(5'-nitro-furfurili- denammino)-idantoina. is condensed with formaldehyde. EXAMPLE 1 Preparation of 5-Hydroxymethyl-1-(5'-nitro-furfurylidenamino)-hydantoin.

A 23,8 gr (0,6 mole) di 1-(5'-nitro-furfurilidenammi- no)-idantoina sospesi in 178 ml di dimetilformammide vengono aggiunti 7,5 ml (0,1 mole) di formalina al 40% e 0,69 ml di piperidina (oppure 0,69 ml di morfolina op- pure 0;72 ml di soluzione 24% di NaOH); si scalda a 70 C per due ore, si raffredda a 15 C, si aggiunge acide acetico glaciale in quantità equivafente alla base impie- gata e si versa quindi la soluzione ottenuta in 600 gr di acqua e ghiaccio allo scopo di avere l'immodiata preci- pitazione di prodotto facilmente filtrabile. To 23.8 g (0.6 mole) of 1-(5'-nitro-furfurylideneamino)-hydantoin suspended in 178 ml of dimethylformamide are added 7.5 ml (0.1 mole) of 40% formalin and 0.69 ml of piperidine (or 0.69 ml of morpholine or 0.72 ml of 24% NaOH solution); it is heated to 70 C for two hours, cooled to 15 C, glacial acetic acid is added in a quantity equivalent to the base used and the solution obtained is then poured into 600 g of water and ice in order to have the immediate precision - easily filterable product pitation.

Il precipitato che si ottiene viene filtrato, lavato con acqua distillata ad essiccato sotte vueto. The precipitate obtained is filtered, washed with distilled water and dried under vacuum.

Resa 97-100% - punto di fusione sul secco 205- 207 C - titolo acidimetrico 99-100%. Yield 97-100% - dry melting point 205-207 C - acidity 99-100%.

Anal@isi elementare Anal@isi elementary

Teorico Trovato C 40,30% 40.35% H 3,01% 3,04% N 20,9% 21,35% 11 composte cosi ettenuto, che è appunto la 5-idrossi- metil-l-(5-nitro-furfurilidenammino)-idautoina, puô es sere, p. e. seconde gli insegnamenti di altro brevette a nome della stessa richiedente, (numéro di demanda 2074/61 del 20.2.61) esterificato e salificato per ettenere p. e. un sale nitrofura-nico idrosolubile dotato di attività chemioterapica. Theoretical Found C 40.30% 40.35% H 3.01% 3.04% N 20.9% 21.35% 11 compound thus obtained, which is precisely the 5-hydroxy- methyl-1-(5-nitro-furfurylidenamino )-idautoin, may be, p. And. according to the teachings of another patent in the name of the same applicant, (application number 2074/61 of 20.2.61) esterified and salified to obtain p. And. a water-soluble nitrofuric salt endowed with chemotherapeutic activity.

Claims (9)

RIVENDICAZIONE Procedimento per la preparazione di un composte ni- trofuronico di formula, CLAIM Process for the preparation of a nitrofuronic compound of the formula, caratterizzato dal fatto che la N-1-(5'-nitro-furfuriliden- ammino)-idantoina, di formula characterized in that N-1-(5'-nitro-furfurylidene-amino)-hydantoin, of the formula viene condensato con aldeide formica. SOTTORIVENDICAZIONI 1. Procedimento secundo la rivendicazione, caratte- rizzato dal fatto che la condensazione si effettua per azione di una base. is condensed with formaldehyde. SUBCLAIMS 1. Process according to the claim, characterized in that the condensation is carried out by the action of a base. 2. Procedimento secundo la sottorivendicazione 1, c.- ratterizzato dal fatto ahe la base utilizzata è una base inorganica. 2. Process according to subclaim 1, characterized in that the base used is an inorganic base. 3. Procedimento secundo la sottorivendicazione 2, caratterizzato dal fatto ahe la base inorganica è un idrato alcalino. 3. Process according to subclaim 2, characterized in that the inorganic base is an alkaline hydrate. 4. Procedimento secundo la sottorivendicazione 1, ca- ratterizzato dal fatto dhe la base utilizzata è una base organisa. 4. Process according to subclaim 1, characterized in that the base used is an organic base. 5. Prooedimento secundo la sottorivendicazione 4, ca- ratterizzato dal fatto che la base utilizzata è la piperidina. 5. Process according to subclaim 4, characterized in that the base used is piperidine. 6. Procedimento secundo la sottorivendicazione 4. na.- ratterizzato dal fatto che la base utilizzata è la morfo- lina. 6. Process according to subclaim 4. na.- characterized in that the base used is morpholine. 7. Procedimento secundo la rivendicazione, caratte- rizzato dal fatto che la reazione viene condotta in un solvente organico compatibile con arqua. 7. Process according to the claim, characterized in that the reaction is carried out in an organic solvent compatible with water. 8. Procedimento secundo la sottorivendicazione 7, ca- ratterizzato da!1 fatto che il solvente organico impiegato è la dimetilformammide. 8. Process according to subclaim 7, characterized in that the organic solvent used is dimethylformamide. 9. Procedimento secundo la @rivendicazione, caratte- rizzato dal fatto che il prodotto della reazione viene se- parato per diluizione della miscela di reazione in arqua tenuta a temperatura di 0-5 C.9. Process according to claim, characterized in that the reaction product is separated by dilution of the reaction mixture in water kept at a temperature of 0-5°C.
CH207561A 1960-02-29 1961-02-20 Process for the synthesis of nitrofuran compound CH438332A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT347360 1960-02-29
IT568160 1960-03-31

Publications (1)

Publication Number Publication Date
CH438332A true CH438332A (en) 1967-06-30

Family

ID=26325403

Family Applications (1)

Application Number Title Priority Date Filing Date
CH207561A CH438332A (en) 1960-02-29 1961-02-20 Process for the synthesis of nitrofuran compound

Country Status (2)

Country Link
CH (1) CH438332A (en)
GB (1) GB975704A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9630934B2 (en) * 2015-02-08 2017-04-25 Mark Quang Nguyen Fumarate compounds, pharmaceutical compositions thereof, and methods of use

Also Published As

Publication number Publication date
GB975704A (en) 1964-11-18

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