CH502375A - Verfahren zur Herstellung neuer Nitrofurylderivate - Google Patents

Verfahren zur Herstellung neuer Nitrofurylderivate

Info

Publication number: CH502375A
Authority: CH; Switzerland
Prior art keywords: nitro; amino; mercapto; furfurylidene; parts
Prior art date: 1966-03-08

Application number

CH332967A

Other languages

German (de)

English (en)

Inventor

Raymond Green Jack

Arton Howarth Graham

William Dr Hoyle

Original Assignee

Ciba Geigy Ag

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.)

1966-03-08

Filing date

1967-03-06

Publication date

1971-01-31

1967-03-06 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1971-01-31 Publication of CH502375A publication Critical patent/CH502375A/de

Links

238000000034 method Methods 0.000 claims abstract description 17
239000002904 solvent Substances 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
239000003795 chemical substances by application Substances 0.000 claims abstract description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
150000004820 halides Chemical class 0.000 claims description 5
230000003009 desulfurizing effect Effects 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229910003439 heavy metal oxide Inorganic materials 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
239000002798 polar solvent Substances 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 11
238000006243 chemical reaction Methods 0.000 abstract description 10
125000003396 thiol group Chemical group [H]S* 0.000 abstract description 6
239000003153 chemical reaction reagent Substances 0.000 abstract description 5
125000001931 aliphatic group Chemical group 0.000 abstract description 4
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract description 4
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 abstract description 4
125000004434 sulfur atom Chemical group 0.000 abstract description 4
SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 abstract description 3
239000002168 alkylating agent Substances 0.000 abstract description 2
229940100198 alkylating agent Drugs 0.000 abstract description 2
229910001385 heavy metal Inorganic materials 0.000 abstract description 2
AYNUCZFIHUUAIZ-UHFFFAOYSA-N s-(2h-triazol-4-yl)thiohydroxylamine Chemical compound NSC1=CNN=N1 AYNUCZFIHUUAIZ-UHFFFAOYSA-N 0.000 abstract 2
230000000507 anthelmentic effect Effects 0.000 abstract 1
239000000921 anthelmintic agent Substances 0.000 abstract 1
239000003242 anti bacterial agent Substances 0.000 abstract 1
230000000844 anti-bacterial effect Effects 0.000 abstract 1
230000000843 anti-fungal effect Effects 0.000 abstract 1
239000003429 antifungal agent Substances 0.000 abstract 1
229940121375 antifungal agent Drugs 0.000 abstract 1
230000001580 bacterial effect Effects 0.000 abstract 1
239000003224 coccidiostatic agent Substances 0.000 abstract 1
230000006866 deterioration Effects 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
230000002538 fungal effect Effects 0.000 abstract 1
230000002209 hydrophobic effect Effects 0.000 abstract 1
238000005470 impregnation Methods 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
229940101209 mercuric oxide Drugs 0.000 abstract 1
230000000813 microbial effect Effects 0.000 abstract 1
239000011368 organic material Substances 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
238000006477 desulfuration reaction Methods 0.000 description 4
230000023556 desulfurization Effects 0.000 description 4
239000007858 starting material Substances 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
DLLBXBCKFUPBJE-UHFFFAOYSA-N 4-amino-1h-1,2,4-triazole-5-thione Chemical compound NN1C=NNC1=S DLLBXBCKFUPBJE-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229910000474 mercury oxide Inorganic materials 0.000 description 2
-1 nitrofuryl derivatives of aminotriazoles Chemical class 0.000 description 2
150000007530 organic bases Chemical group 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
LPYIXHHGKPBPCF-UHFFFAOYSA-N acetic acid;5-nitrofuran-2-carbaldehyde Chemical compound CC(O)=O.CC(O)=O.[O-][N+](=O)C1=CC=C(C=O)O1 LPYIXHHGKPBPCF-UHFFFAOYSA-N 0.000 description 1
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Coloring (AREA)

CH332967A 1966-03-08 1967-03-06 Verfahren zur Herstellung neuer Nitrofurylderivate CH502375A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB998966A GB1110469A (en)	1966-03-08	1966-03-08	Nitrofuryl derivatives of aminotriazoles

Publications (1)

Publication Number	Publication Date
CH502375A true CH502375A (de)	1971-01-31

Family

ID=9882498

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH332967A CH502375A (de)	1966-03-08	1967-03-06	Verfahren zur Herstellung neuer Nitrofurylderivate

Country Status (7)

Country	Link
AT (1)	AT266106B (da)
CH (1)	CH502375A (da)
DE (1)	DE1695009A1 (da)
DK (1)	DK112172B (da)
ES (1)	ES337701A1 (da)
GB (1)	GB1110469A (da)
NL (1)	NL6703582A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0657437A1 (de) *	1993-12-10	1995-06-14	Bayer Ag	Verfahren und neue Zwischenprodukte zur Herstellung von Triazolinonen

1966
- 1966-03-08 GB GB998966A patent/GB1110469A/en not_active Expired
1967
- 1967-03-06 CH CH332967A patent/CH502375A/de not_active IP Right Cessation
- 1967-03-07 NL NL6703582A patent/NL6703582A/xx unknown
- 1967-03-07 ES ES337701A patent/ES337701A1/es not_active Expired
- 1967-03-07 AT AT216167A patent/AT266106B/de active
- 1967-03-07 DK DK117467A patent/DK112172B/da unknown
- 1967-03-07 DE DE19671695009 patent/DE1695009A1/de active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0657437A1 (de) *	1993-12-10	1995-06-14	Bayer Ag	Verfahren und neue Zwischenprodukte zur Herstellung von Triazolinonen

Also Published As

Publication number	Publication date
DK112172B (da)	1968-11-18
NL6703582A (da)	1967-09-11
ES337701A1 (es)	1968-03-01
GB1110469A (en)	1968-04-18
AT266106B (de)	1968-11-11
DE1695009A1 (de)	1971-04-08

Legal Events

Date	Code	Title	Description
1973-10-15	PL	Patent ceased

Publication	Publication Date	Title
EP1343770B1 (de)	2009-05-06	Lithium-komplexe von n-(1-hydroxymethyl-2,3-dihydroxypropyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecan, deren herstellung und verwendung
EP0131776A2 (de)	1985-01-23	Verfahren zur Herstellung von Thiazolyl-2-sulfenamiden
US3448119A (en)	1969-06-03	Producing tetramethylisoindolenine by heating acetonylacetone in aqueous ammonium salt
CH502375A (de)	1971-01-31	Verfahren zur Herstellung neuer Nitrofurylderivate
DE1251327B (de)	1967-10-05	Verfahren zur Her Stellung von in 5 Stellung substituierten 1 Aryl-lH-tetrazolen
DE915809C (de)	1954-07-29	Verfahren zur Herstellung von heterocyclischen Sulfonamiden
DE1795344B2 (de)	1976-05-06	Verfahren zur herstellung von 3-aminoisothiazolen
US3133107A (en)	1964-05-12	Semicarbazide hexafluoroarsenate
DE832891C (de)	1952-03-03	Verfahren zur Herstellung von Thiosemicarbaziden
US3597440A (en)	1971-08-03	Salts of isoperthiocyanic acid
US2179984A (en)	1939-11-14	Process fob the manufacture of
US2870144A (en)	1959-01-20	3-furfurylidene-aminmo-1, 2, 4-triazole and process for producing same
DE839349C (de)	1952-05-19	Verfahren zur Herstellung von Thiosemicarbaziden
DE2413938C2 (da)	1987-12-03
DE528113C (de)	1931-06-25	Verfahren zur Darstellung von Pyridinarsinsaeuren
AT258910B (de)	1967-12-27	Verfahren zur Herstellung von Benzo-dihydro-thiadiazin-Derivaten
US3014919A (en)	1961-12-26	Dithiocarbamate salts of dodecahydrocarbazole
AT206902B (de)	1960-01-11	Verfahren zur Herstellung neuer Monocarbaminsäureester von disubstituierten Butandiolen
AT206444B (de)	1959-11-25	Verfahren zur Herstellung von neuen Pyridazinderivaten
AT204552B (de)	1959-07-25	Verfahren zur Herstellung von neuen, heterocyclischen Bis-sulfonamiden
AT228793B (de)	1963-08-12	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
DE950639C (de)	1956-10-11	Verfahren zur Herstellung von ausschliesslich in 5-Stellung substituierten 2-Mercapto-1-ox-3, 4-diazolen
AT235838B (de)	1964-09-25	Verfahren zur Herstellung von neuen Derivaten des 2, 3-Dimercaptochinoxalins
US3248367A (en)	1966-04-26	3-morpholinopropiophenone hexafluorophosphate
AT227696B (de)	1963-06-10	Verfahren zur Herstellung von 2-Amino-oxazolen

CH502375A - Verfahren zur Herstellung neuer Nitrofurylderivate - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=9882498

Family Applications (1)

Country Status (7)

Cited By (1)

Cited By (1)

Also Published As

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Legal Events