CH410962A - Verfahren zur Herstellung von Phenylazopyrimidinen - Google Patents

Verfahren zur Herstellung von Phenylazopyrimidinen

Info

Publication number: CH410962A
Authority: CH; Switzerland
Prior art keywords: parts; hydrazino; mixture; hydrogen; alkyl
Prior art date: 1959-07-03

Application number

CH747860A

Other languages

German (de)

English (en)

Inventor

Hodgson Laird Alan

Kenneth Landquist Justus

William Langley Bernard

Original Assignee

Ici Ltd

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.)

1959-07-03

Filing date

1960-07-01

Publication date

1966-04-15

1960-07-01 Application filed by Ici Ltd filed Critical Ici Ltd

1966-04-15 Publication of CH410962A publication Critical patent/CH410962A/de

Links

ZMOHEJSEXHOUTG-UHFFFAOYSA-N (4-phenylpyrimidin-2-yl)-pyrimidin-2-yldiazene Chemical class C1=CC=CC=C1C1=CC=NC(N=NC=2N=CC=CN=2)=N1 ZMOHEJSEXHOUTG-UHFFFAOYSA-N 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 6
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 12
-1 alkyl radical Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
ZHNIRIANAAPGDH-UHFFFAOYSA-N 6-hydrazinyl-1h-pyrimidine-2,4-dione Chemical compound NNC1=CC(=O)NC(=O)N1 ZHNIRIANAAPGDH-UHFFFAOYSA-N 0.000 claims description 8
229940005561 1,4-benzoquinone Drugs 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
LUWPFMIHXOPDBK-UHFFFAOYSA-N 2-amino-6-hydrazinyl-1h-pyrimidin-4-one Chemical compound NNC1=CC(=O)N=C(N)N1 LUWPFMIHXOPDBK-UHFFFAOYSA-N 0.000 claims description 5
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
229910015900 BF3 Inorganic materials 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000003701 inert diluent Substances 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
229910052751 metal Chemical class 0.000 claims description 2
239000002184 metal Chemical class 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical compound NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
239000007858 starting material Substances 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
HOCVPMXPWHBCSK-UHFFFAOYSA-N 6-chloro-5-methyl-1h-pyrimidine-2,4-dione Chemical compound CC1=C(Cl)NC(=O)NC1=O HOCVPMXPWHBCSK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
WFCXSZSLXQJFDD-UHFFFAOYSA-N chembl1742076 Chemical compound C1=CC(O)=CC=C1N=NC1=CC(=O)NC(=O)N1 WFCXSZSLXQJFDD-UHFFFAOYSA-N 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
WOGWYSWDBYCVDY-UHFFFAOYSA-N 2-chlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C=CC1=O WOGWYSWDBYCVDY-UHFFFAOYSA-N 0.000 description 2
KPSACJAXUZXHMO-UHFFFAOYSA-N 6-hydrazinyl-5-methyl-1H-pyrimidine-2,4-dione Chemical compound N(N)C1=NC(=NC(=C1C)O)O KPSACJAXUZXHMO-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
REZVRJZHTFIXDK-UHFFFAOYSA-N chembl1886015 Chemical compound N1C(N)=NC(=O)C=C1N=NC1=CC=C(O)C=C1 REZVRJZHTFIXDK-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
RAAWOIFHWPNICM-UHFFFAOYSA-N 2-amino-4-[(3-chloro-4-hydroxyphenyl)diazenyl]-1H-pyrimidin-6-one Chemical compound NC1=NC(=CC(=N1)N=NC1=CC(=C(C=C1)O)Cl)O RAAWOIFHWPNICM-UHFFFAOYSA-N 0.000 description 1
VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 1
NBHAZVWKRHTWRW-UHFFFAOYSA-N 2-propylcyclohexa-2,5-diene-1,4-dione Chemical compound CCCC1=CC(=O)C=CC1=O NBHAZVWKRHTWRW-UHFFFAOYSA-N 0.000 description 1
FHDGSYIDVKPQAY-UHFFFAOYSA-N 4-chloro-2,6-dimethoxy-5-methylpyrimidine Chemical compound COC1=NC(Cl)=C(C)C(OC)=N1 FHDGSYIDVKPQAY-UHFFFAOYSA-N 0.000 description 1
PPECMSQKAVWRSP-UHFFFAOYSA-N 4-chloro-6-hydrazinylpyrimidin-2-amine Chemical compound NNC1=CC(Cl)=NC(N)=N1 PPECMSQKAVWRSP-UHFFFAOYSA-N 0.000 description 1
VFKWOJAARMMQRW-UHFFFAOYSA-N 6-[(3-chloro-4-hydroxyphenyl)diazenyl]-1H-pyrimidine-2,4-dione Chemical compound OC1=NC(=CC(=N1)N=NC1=CC(=C(C=C1)O)Cl)O VFKWOJAARMMQRW-UHFFFAOYSA-N 0.000 description 1
RJXOPDWDFGZZLB-UHFFFAOYSA-N 6-[(4-hydroxy-3-methylphenyl)diazenyl]-1H-pyrimidine-2,4-dione Chemical compound CC1=C(O)C=CC(=C1)N=NC1=CC(O)=NC(O)=N1 RJXOPDWDFGZZLB-UHFFFAOYSA-N 0.000 description 1
UBLCFJXUFHOWLB-UHFFFAOYSA-N 6-[(4-hydroxy-3-propylphenyl)diazenyl]-1H-pyrimidine-2,4-dione Chemical compound OC1=NC(=CC(=N1)N=NC1=CC(=C(C=C1)O)CCC)O UBLCFJXUFHOWLB-UHFFFAOYSA-N 0.000 description 1
PKUFNWPSFCOSLU-UHFFFAOYSA-N 6-chloro-1h-pyrimidine-2,4-dione Chemical compound ClC1=CC(=O)NC(=O)N1 PKUFNWPSFCOSLU-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
MRNRBQDGZFVHCB-UHFFFAOYSA-N OC1=NC(=C(C(=N1)N=NC1=CC=C(C=C1)O)C)O Chemical compound OC1=NC(=C(C(=N1)N=NC1=CC=C(C=C1)O)C)O MRNRBQDGZFVHCB-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
241000295644 Staphylococcaceae Species 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000004396 mastitis Diseases 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH747860A 1959-07-03 1960-07-01 Verfahren zur Herstellung von Phenylazopyrimidinen CH410962A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB22904/59A GB876601A (en)	1959-07-03	1959-07-03	Pyrimidine derivatives

Publications (1)

Publication Number	Publication Date
CH410962A true CH410962A (de)	1966-04-15

Family

ID=10186945

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH747860A CH410962A (de)	1959-07-03	1960-07-01	Verfahren zur Herstellung von Phenylazopyrimidinen

Country Status (3)

Country	Link
CH (1)	CH410962A (fr)
FR (1)	FR377M (fr)
GB (1)	GB876601A (fr)

1959
- 1959-07-03 GB GB22904/59A patent/GB876601A/en not_active Expired
1960
- 1960-07-01 CH CH747860A patent/CH410962A/de unknown
- 1960-08-29 FR FR837072A patent/FR377M/fr not_active Expired

Also Published As

Publication number	Publication date
FR377M (fr)	1961-04-04
GB876601A (en)	1961-09-06

Publication	Publication Date	Title
DE1470082C3 (de)	1974-08-22	Verfahren zur Herstellung von in der 2-Stellung substituierten Benzimidazolen
CH493528A (de)	1970-07-15	Verfahren zur Herstellung neuer substituierter Aminopyrimidine
DE1445186C3 (de)	1974-11-07	3,3'-Di-2-imidazolin-2-yl-carbanilid
DE1904894C3 (de)	1983-06-16	Verfahren zur Herstellung von 3-Amino-4-carboxamido-pyrazolen
DE1545607A1 (de)	1969-12-04	Verfahren zur Herstellung neuer 5-Nitrofuran-Derivate
CH410962A (de)	1966-04-15	Verfahren zur Herstellung von Phenylazopyrimidinen
DE1966203C3 (de)	1980-10-09	2,3-Dioxo-4-(R',R")-aminomethylpyrrolidine und Verfahren zu ihrer Herstellung
DE1445438C (fr)	1973-08-30
DE1235929B (de)	1967-03-09	Verfahren zur Herstellung von 2-(2'-Pyrazinyl)-benzimidazol und seinen Salzen
AT233010B (de)	1964-04-25	Verfahren zur Herstellung von neuen Benzo-dihydro-1, 2, 4-thiadiazin-1, 1-dioxyden
DE1284426B (de)	1968-12-05	4-(5'-Nitro-2'-furfuryliden-amino)-1, 2, 4-triazolone-(5) und Verfahren zu ihrer Herstellung
AT229874B (de)	1963-10-25	Verfahren zur Herstellung von neuen (5- oder 6)-Alkyl- und 5, 6-Dialkyl-3-alkoxy-pyrazinen
AT278037B (de)	1970-01-26	Verfahren zur Herstellung neuer borhaltiger heterocyclischer Verbindungen
DE864555C (de)	1953-01-26	Verfahren zur Herstellung von 2, 4-Diamino-5-aryloxypyrimidinen
DE945237C (de)	1956-07-05	Verfahren zur Herstellung von Pyrrolinonen
AT239440B (de)	1965-04-12	Verfahren zur Herstellung von neuen Derivaten der 6-Amino-Penicillansäure
AT236941B (de)	1964-11-25	Verfahren zur Herstellung von neuen substituierten Benzimidazolen und deren Säureadditionssalzen
DE1670378C (de)	1972-09-21	Verfahren zur Herstellung des Salzes aus4-n-Butyl-3,5-dioxo-l,2-diphenylpyrazolidin und dem beta-Diäthylamino-äthylamid der p-Chlorphenoxyessigsäure
DE1131686B (de)	1962-06-20	Verfahren zur Herstellung von Phenylazopyrimidinderivaten
DE1921340C3 (de)	1974-10-31	In 4-Stellung substituierte 2-Phenyl-5-haIogen-pyrimidine
DE1219941B (de)	1966-06-30	Verfahren zur Herstellung von in 7-Stellung substituierten 2, 4, 6-Triaminopteridinen
DE1670317A1 (de)	1971-02-25	Neue 5-Nitrofuran-Derivate und Verfahren zur Herstellung derselben
DE2418435A1 (de)	1975-10-30	Nitroimidazolyl-triazolo-pyridazine und verfahren zu ihrer herstellung
DE1100637B (de)	1961-03-02	Verfahren zur Herstellung von Alkyleniminoalkylguanidinen, deren Acylverbindungen, Salzen und quaternaeren Ammoniumverbindungen
DE1088963B (de)	1960-09-15	Verfahren zur Herstellung von p-Benzochinon-monoguanylhydrazon-monothiazolylhydrazonen