DE4024259A1 - Verfahren zur herstellung von substituierten zyklischen amidinen - Google Patents
Verfahren zur herstellung von substituierten zyklischen amidinenInfo
- Publication number
- DE4024259A1 DE4024259A1 DE19904024259 DE4024259A DE4024259A1 DE 4024259 A1 DE4024259 A1 DE 4024259A1 DE 19904024259 DE19904024259 DE 19904024259 DE 4024259 A DE4024259 A DE 4024259A DE 4024259 A1 DE4024259 A1 DE 4024259A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- hydrogen sulfide
- nitrile
- diamine
- substituted
- 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.)
- Granted
Links
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 28
- -1 cyclic amidine Chemical class 0.000 title claims abstract description 14
- 150000001412 amines Chemical class 0.000 title description 5
- 150000004985 diamines Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000003464 sulfur compounds Chemical class 0.000 claims description 3
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical group [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 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 class [H]* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000003825 pressing Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 5
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 229920000647 polyepoxide Polymers 0.000 abstract description 2
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 150000002462 imidazolines Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- VWSLLSXLURJCDF-UHFFFAOYSA-N 2-methyl-4,5-dihydro-1h-imidazole Chemical compound CC1=NCCN1 VWSLLSXLURJCDF-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- UWEDTBYOSGZWDY-UHFFFAOYSA-N S.C(CN)N Chemical compound S.C(CN)N UWEDTBYOSGZWDY-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001284 azanium sulfanide Substances 0.000 description 1
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 1
- ZOSAYFDMPYAZTB-UHFFFAOYSA-N bis(prop-2-enyl)cyanamide Chemical compound C=CCN(C#N)CC=C ZOSAYFDMPYAZTB-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011049 pearl Substances 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
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000000246 remedial effect Effects 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JMPVZWBJWHQJDD-UHFFFAOYSA-N sulfur tetrachloride Chemical compound ClS(Cl)(Cl)Cl JMPVZWBJWHQJDD-UHFFFAOYSA-N 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said 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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/14—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904024259 DE4024259A1 (de) | 1990-07-31 | 1990-07-31 | Verfahren zur herstellung von substituierten zyklischen amidinen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904024259 DE4024259A1 (de) | 1990-07-31 | 1990-07-31 | Verfahren zur herstellung von substituierten zyklischen amidinen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE4024259A1 true DE4024259A1 (de) | 1992-02-06 |
| DE4024259C2 DE4024259C2 (enExample) | 1993-08-12 |
Family
ID=6411359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19904024259 Granted DE4024259A1 (de) | 1990-07-31 | 1990-07-31 | Verfahren zur herstellung von substituierten zyklischen amidinen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE4024259A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0574795A1 (de) * | 1992-06-17 | 1993-12-22 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Pyrimidinen |
| WO2018181001A1 (ja) * | 2017-03-31 | 2018-10-04 | 三菱瓦斯化学株式会社 | アミノメチル基を有するフェニルイミダゾリン化合物若しくはその塩、又は、アミノメチル基を有するフェニルテトラヒドロピリミジン化合物若しくはその塩、及び、それらの化合物又はそれらの塩の製造方法 |
| CN117466818A (zh) * | 2023-12-26 | 2024-01-30 | 潍坊弘润新材料有限公司 | 一种无溶剂法制备2-芳基咪唑啉类化合物的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2512513A1 (de) * | 1975-03-21 | 1976-10-07 | Basf Ag | Verfahren zur herstellung von 2-imidazolinen |
-
1990
- 1990-07-31 DE DE19904024259 patent/DE4024259A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2512513A1 (de) * | 1975-03-21 | 1976-10-07 | Basf Ag | Verfahren zur herstellung von 2-imidazolinen |
Non-Patent Citations (1)
| Title |
|---|
| PL 1 43 788, 1, zitiert in Chem. Abstr. 112, 35878a, 1990 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0574795A1 (de) * | 1992-06-17 | 1993-12-22 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Pyrimidinen |
| US5362875A (en) * | 1992-06-17 | 1994-11-08 | Basf Aktiengesellschaft | Preparation of pyrimidines |
| WO2018181001A1 (ja) * | 2017-03-31 | 2018-10-04 | 三菱瓦斯化学株式会社 | アミノメチル基を有するフェニルイミダゾリン化合物若しくはその塩、又は、アミノメチル基を有するフェニルテトラヒドロピリミジン化合物若しくはその塩、及び、それらの化合物又はそれらの塩の製造方法 |
| CN110234630A (zh) * | 2017-03-31 | 2019-09-13 | 三菱瓦斯化学株式会社 | 具有氨基甲基的苯基咪唑啉化合物或其盐、或者具有氨基甲基的苯基四氢嘧啶化合物或其盐、及这些化合物或这些盐的制造方法 |
| JPWO2018181001A1 (ja) * | 2017-03-31 | 2020-02-06 | 三菱瓦斯化学株式会社 | アミノメチル基を有するフェニルイミダゾリン化合物若しくはその塩、又は、アミノメチル基を有するフェニルテトラヒドロピリミジン化合物若しくはその塩、及び、それらの化合物又はそれらの塩の製造方法 |
| TWI749201B (zh) * | 2017-03-31 | 2021-12-11 | 日商三菱瓦斯化學股份有限公司 | 具有胺甲基之苯基咪唑啉化合物或其鹽、或具有胺甲基之苯基四氫嘧啶化合物或其鹽、以及此等化合物或此等鹽的製造方法 |
| US11198676B2 (en) | 2017-03-31 | 2021-12-14 | Mitsubishi Gas Chemical Company, Inc. | Phenyl imidazoline compound having aminomethyl group or salt thereof, or phenyl tetrahydropyrimidine compound having aminomethyl group or salt thereof, and production method for such compounds or salts thereof |
| CN110234630B (zh) * | 2017-03-31 | 2023-02-03 | 三菱瓦斯化学株式会社 | 具有氨基甲基的苯基咪唑啉化合物或其盐及其制造方法 |
| CN117466818A (zh) * | 2023-12-26 | 2024-01-30 | 潍坊弘润新材料有限公司 | 一种无溶剂法制备2-芳基咪唑啉类化合物的方法 |
| CN117466818B (zh) * | 2023-12-26 | 2024-04-26 | 潍坊弘润新材料有限公司 | 一种无溶剂法制备2-芳基咪唑啉类化合物的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4024259C2 (enExample) | 1993-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2811764A1 (de) | Neue imidazol-isocyanursaeure-addukte sowie verfahren zu deren herstellung und anwendung | |
| DE2826452A1 (de) | Verfahren zur herstellung von substituierten guanidinen | |
| DE4024259A1 (de) | Verfahren zur herstellung von substituierten zyklischen amidinen | |
| DE3001752A1 (de) | Verfahren zur herstellung von 8(alpha)-substituierten 6-methylergolinen | |
| DE2758171C2 (de) | Verfahren zur Herstellung von Isopropyl-, tert.-Butyl- oder Cyclohexylisocyanat | |
| DE943225C (de) | Verfahren zur Herstellung aromatischer Nitrile | |
| EP0971886B1 (de) | Verfahren zur herstellung von n-alkyl-n'-nitroguanidinen | |
| DE858402C (de) | Verfahren zur Herstellung heterocyclischer Verbindungen | |
| DE2446489A1 (de) | Verfahren zur herstellung von bis(2-cyanoaethyl)-aethylendiamin | |
| DD148952A1 (de) | Verfahren zur herstellung von blutdrucksenkendem 6,7-dimethoxy-4-amino-2- eckige klammer auf 4-(2-furoyl)-1-piperazinyl eckige klammer zu chinazolinhydrochlorid | |
| DE2512513A1 (de) | Verfahren zur herstellung von 2-imidazolinen | |
| DE1445581A1 (de) | N-[5-Methyloxazolinyl-(2)]-N'-aryl-Harnstoffderivate und Verfahren zu deren Herstellung | |
| DE2654928A1 (de) | Verfahren zur herstellung von n-methylierten bzw. n-methyl-harnstoffen | |
| DE1126392B (de) | Verfahren zur Herstellung cyclischer Harnstoffe und Thioharnstoffe | |
| DE1190944B (de) | Verfahren zur Herstellung von heterocyclischen N-Vinylverbindungen | |
| DE3007530C2 (enExample) | ||
| AT313298B (de) | Verfahren zur Herstellung von neuen Pyrrolidin-N-carbonsäure-halogenaniliden | |
| DE1965004C3 (de) | Verfahren zur Herstellung von N-Acyl-aminocyclohexancarbonsäurenitrilen | |
| DE1063602B (de) | Verfahren zur Herstellung von 1, 5, 5-trialkylsubstituierten delta 3,4-Thiazolinen | |
| DD150895A1 (de) | Verfahren zur herstellung von substituierten nitrobenzoheterozyklen | |
| DE1693039A1 (de) | Verfahren zur Herstellung von Malonsaeuredinitril | |
| DE637730C (de) | Verfahren zur Herstellung von N-Alkylderivaten des Ammoniaks | |
| DE2944953C2 (de) | Verfahren zur Herstellung von N,N'-1,1-Dimethyltrimethylen-bis-benzamid | |
| DE678194C (de) | Verfahren zur Herstellung von Verbindungen von Mercaptothiazolen | |
| DE1064944B (de) | Verfahren zur Herstellung von Harnstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |