CH421113A - Verfahren zur Herstellung von Mercaptochinoxalinen - Google Patents

Verfahren zur Herstellung von Mercaptochinoxalinen

Info

Publication number: CH421113A
Authority: CH; Switzerland
Prior art keywords: carbonic acid; salts; acids; thiol; derivatives
Prior art date: 1960-11-25

Application number

CH1340161A

Other languages

German (de)

English (en)

Inventor

Klaus Dr Sasse

Eberhardt Dr Degener

Carl-Wolfgang Dr Schellhammer

Richard Dr Wegler

Original Assignee

Bayer 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.)

1960-11-25

Filing date

1961-11-17

Publication date

1966-09-30

1961-11-17 Application filed by Bayer Ag filed Critical Bayer Ag

1966-09-30 Publication of CH421113A publication Critical patent/CH421113A/de

Links

238000000034 method Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 4
INQXGZFDGDSRIF-UHFFFAOYSA-N 1h-quinoxaline-2-thione Chemical class C1=CC=CC2=NC(S)=CN=C21 INQXGZFDGDSRIF-UHFFFAOYSA-N 0.000 title description 3
-1 thiol carboxylic acids Chemical class 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 11
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
238000000354 decomposition reaction Methods 0.000 claims description 3
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
150000004662 dithiols Chemical class 0.000 claims description 2
150000003566 thiocarboxylic acids Chemical class 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 10
239000002253 acid Substances 0.000 description 9
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
239000000203 mixture Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000000047 product Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
YFBUDXNMBTUSOC-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dithione Chemical compound C1=CC=C2NC(=S)C(=S)NC2=C1 YFBUDXNMBTUSOC-UHFFFAOYSA-N 0.000 description 2
SPSSDDOTEZKOOV-UHFFFAOYSA-N 2,3-dichloroquinoxaline Chemical compound C1=CC=C2N=C(Cl)C(Cl)=NC2=C1 SPSSDDOTEZKOOV-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
FHFIFDIROVVAEK-UHFFFAOYSA-N carbonotrithioic acid quinoxaline Chemical compound C(S)(S)=S.N1=CC=NC2=CC=CC=C12 FHFIFDIROVVAEK-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000007858 starting material Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
TWKKUWBBCHHMLT-UHFFFAOYSA-N disodium;sulfide;trihydrate Chemical compound O.O.O.[Na+].[Na+].[S-2] TWKKUWBBCHHMLT-UHFFFAOYSA-N 0.000 description 1
150000002023 dithiocarboxylic acids Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH1340161A 1960-11-25 1961-11-17 Verfahren zur Herstellung von Mercaptochinoxalinen CH421113A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0032621		1960-11-25

Publications (1)

Publication Number	Publication Date
CH421113A true CH421113A (de)	1966-09-30

Family

ID=7094711

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1340161A CH421113A (de)	1960-11-25	1961-11-17	Verfahren zur Herstellung von Mercaptochinoxalinen

Country Status (3)

Country	Link
AT (1)	AT240856B (da)
CH (1)	CH421113A (da)
DK (1)	DK103444C (da)

1961
- 1961-11-17 CH CH1340161A patent/CH421113A/de unknown
- 1961-11-22 DK DK466461A patent/DK103444C/da active
- 1961-11-23 AT AT885361A patent/AT240856B/de active

Also Published As

Publication number	Publication date
DK103444C (da)	1966-01-03
AT240856B (de)	1965-06-25

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