DE1168897B - Verfahren zur Herstellung von Thioformaryliden - Google Patents
Verfahren zur Herstellung von ThioformarylidenInfo
- Publication number
- DE1168897B DE1168897B DEB67107A DEB0067107A DE1168897B DE 1168897 B DE1168897 B DE 1168897B DE B67107 A DEB67107 A DE B67107A DE B0067107 A DEB0067107 A DE B0067107A DE 1168897 B DE1168897 B DE 1168897B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dimethylformamidine
- hydrogen sulfide
- formamidines
- formamidine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 14
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 14
- -1 alkyl radical Chemical class 0.000 claims description 13
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 150000003840 hydrochlorides Chemical class 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- UNRRVOATHRPYDX-UHFFFAOYSA-N n-phenylmethanethioamide Chemical compound S=CNC1=CC=CC=C1 UNRRVOATHRPYDX-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical compound SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 description 2
- ZQUVDXMUKIVNOW-UHFFFAOYSA-N n,n'-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1NC=NC1=CC=CC=C1 ZQUVDXMUKIVNOW-UHFFFAOYSA-N 0.000 description 2
- SRPCLECGIYMIMN-UHFFFAOYSA-N n,n-dimethyl-n'-phenylmethanimidamide Chemical compound CN(C)C=NC1=CC=CC=C1 SRPCLECGIYMIMN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- JHXPCSYIECUNMQ-UHFFFAOYSA-M potassium methanedithioate Chemical compound [K+].[S-]C=S JHXPCSYIECUNMQ-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZXLRJWTXAGGHHF-UHFFFAOYSA-N [Cl-].C(=O)(O)C1=CC=C(C=C1)[NH+]=CN(C)C Chemical compound [Cl-].C(=O)(O)C1=CC=C(C=C1)[NH+]=CN(C)C ZXLRJWTXAGGHHF-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical compound Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RFCMTCIUSXIYQH-UHFFFAOYSA-N dimethyl(phenyliminomethyl)azanium;chloride Chemical compound Cl.CN(C)C=NC1=CC=CC=C1 RFCMTCIUSXIYQH-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- GTCCMGFBIWUBLQ-UHFFFAOYSA-N formamide;hydrochloride Chemical compound Cl.NC=O GTCCMGFBIWUBLQ-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BZBSXSKRUISGJM-UHFFFAOYSA-N n'-(3-chlorophenyl)-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=CC=CC(Cl)=C1 BZBSXSKRUISGJM-UHFFFAOYSA-N 0.000 description 1
- FGJAUZBFVHDGFB-UHFFFAOYSA-N n'-(3-chlorophenyl)-n,n-dimethylmethanimidamide;hydrochloride Chemical compound Cl.CN(C)C=NC1=CC=CC(Cl)=C1 FGJAUZBFVHDGFB-UHFFFAOYSA-N 0.000 description 1
- KEHWKNJZSFYKEM-UHFFFAOYSA-N n'-(4-methoxyphenyl)-n,n-dimethylmethanimidamide Chemical compound COC1=CC=C(N=CN(C)C)C=C1 KEHWKNJZSFYKEM-UHFFFAOYSA-N 0.000 description 1
- NGBFYNDQAWVHQR-UHFFFAOYSA-N n'-(4-methoxyphenyl)-n,n-dimethylmethanimidamide;hydrochloride Chemical compound Cl.COC1=CC=C(N=CN(C)C)C=C1 NGBFYNDQAWVHQR-UHFFFAOYSA-N 0.000 description 1
- YNDWGMJUIJQILC-UHFFFAOYSA-N n,n-diethyl-n'-phenylmethanimidamide Chemical compound CCN(CC)C=NC1=CC=CC=C1 YNDWGMJUIJQILC-UHFFFAOYSA-N 0.000 description 1
- LQXZCPNRKDUVET-UHFFFAOYSA-N n,n-dimethyl-n'-(3-nitrophenyl)methanimidamide Chemical compound CN(C)C=NC1=CC=CC([N+]([O-])=O)=C1 LQXZCPNRKDUVET-UHFFFAOYSA-N 0.000 description 1
- VBLAVCCSDMDOCP-UHFFFAOYSA-N n,n-dimethyl-n'-(4-nitrophenyl)methanimidamide Chemical compound CN(C)C=NC1=CC=C([N+]([O-])=O)C=C1 VBLAVCCSDMDOCP-UHFFFAOYSA-N 0.000 description 1
- QRZCCDBDBYCVDU-UHFFFAOYSA-N n,n-dimethylformamide;dihydrochloride Chemical compound Cl.Cl.CN(C)C=O QRZCCDBDBYCVDU-UHFFFAOYSA-N 0.000 description 1
- FJLHLDBEZKTSOK-UHFFFAOYSA-N n-ethyl-n-methylformamide Chemical compound CCN(C)C=O FJLHLDBEZKTSOK-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/205—Dyes with an unsaturated C on the N atom attached to the nucleus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/16—Benz-diazabenzanthrones, e.g. anthrapyrimidones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE631778D BE631778A (en:Method) | 1962-05-04 | ||
| DEB67107A DE1168897B (de) | 1962-05-04 | 1962-05-04 | Verfahren zur Herstellung von Thioformaryliden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB67107A DE1168897B (de) | 1962-05-04 | 1962-05-04 | Verfahren zur Herstellung von Thioformaryliden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1168897B true DE1168897B (de) | 1964-04-30 |
Family
ID=6975391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB67107A Pending DE1168897B (de) | 1962-05-04 | 1962-05-04 | Verfahren zur Herstellung von Thioformaryliden |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE631778A (en:Method) |
| DE (1) | DE1168897B (en:Method) |
-
0
- BE BE631778D patent/BE631778A/xx unknown
-
1962
- 1962-05-04 DE DEB67107A patent/DE1168897B/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE631778A (en:Method) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0101407B1 (de) | Verfahren zur Herstellung von herbiziden und pflanzenwuchsregulierenden Sulfonylharnstoffen und neue Sulfonylcarbamate als Zwischenprodukte | |
| DE2024909B2 (de) | Verfahren zur herstellung von n-hydroxyalkyl-perfluoralkansulfonamiden und einige n,n-bis-(hydroxyalkyl)-perfluor-alkansulfonamide | |
| DE2858737C2 (en:Method) | ||
| DE1445675C3 (de) | Pyridylharnstoffe und Verfahren zu ihrer Herstellung | |
| DE1168897B (de) | Verfahren zur Herstellung von Thioformaryliden | |
| EP0971907B1 (de) | Verfahren zur herstellung von 1,3-disubstituierten 2-nitroguanidinen | |
| DE1213835B (de) | Verfahren zur Herstellung substituierter Semicarbazide | |
| DE1932297C3 (de) | Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureestern | |
| DE2438077A1 (de) | Verfahren zur herstellung von propanolaminderivaten und nach dem verfahren hergestellte propanolaminderivate | |
| DE970463C (de) | Verfahren zur Herstellung von Kondensationsprodukten | |
| DE2417669A1 (de) | Verfahren zur herstellung von n(halogenaryl)-n',n'-dialkylamidinen | |
| DE1240873B (de) | Verfahren zur Herstellung von 4-Halogen-5-sulfamylanthranilsaeure-hydroxamiden | |
| DE1156403B (de) | Verfahren zur Herstellung von Sulfonsaeureamid-N-sulfensaeurechloriden | |
| DE963058C (de) | Verfahren zur Herstellung von Harnstoffgruppen enthaltenden Sulfonamiden | |
| DE1910295A1 (de) | Verfahren zur Herstellung von 1-Naphthyl-N-alkyl-carbamaten | |
| EP0000573B1 (de) | Verfahren zur Herstellung von Diaminen mit einer Thioäthergruppe | |
| DE1443913C (de) | Verfahren zur Herstellung von N Cyanoiminokohlensaureesteramiden | |
| AT218534B (de) | Verfahren zur Herstellung von neuen substituierten Harnstoffen | |
| DE2137649B2 (en:Method) | ||
| DE1231246B (de) | Verfahren zur Herstellung von Arylhydrazonen von alpha-Ketocarbonsaeureamiden | |
| DE2237549B2 (de) | Mycophenolsäureester-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1226589B (de) | Verfahren zur Herstellung von Imidazolidonen | |
| DE1643983A1 (de) | Verfahren zur Herstellung von N-sulfonyl-carbonamidtert,Amin-Addukten | |
| DD246539A1 (de) | Verfahren zur herstellung symmetrischer kohlensaeurediester | |
| DE2208325A1 (en:Method) |