DE2454107B2 - Verfahren zur herstellung von harnstoffen, acylharnstoffen und sulfonylharnstoffen - Google Patents
Verfahren zur herstellung von harnstoffen, acylharnstoffen und sulfonylharnstoffenInfo
- Publication number
- DE2454107B2 DE2454107B2 DE19742454107 DE2454107A DE2454107B2 DE 2454107 B2 DE2454107 B2 DE 2454107B2 DE 19742454107 DE19742454107 DE 19742454107 DE 2454107 A DE2454107 A DE 2454107A DE 2454107 B2 DE2454107 B2 DE 2454107B2
- Authority
- DE
- Germany
- Prior art keywords
- group
- general formula
- hydrogen atom
- urea
- alkyl group
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 229940100389 Sulfonylurea Drugs 0.000 title claims description 7
- 150000007945 N-acyl ureas Chemical class 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 3
- 239000004202 carbamide Substances 0.000 title description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 235000013877 carbamide Nutrition 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims 4
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 150000001912 cyanamides Chemical class 0.000 description 6
- 238000006434 Ritter amidation reaction Methods 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OXCSCSQUAKQKMY-UHFFFAOYSA-N 1-tert-butyl-3-phenylurea Chemical compound CC(C)(C)NC(=O)NC1=CC=CC=C1 OXCSCSQUAKQKMY-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- IGPHOCUPTPJKQY-UHFFFAOYSA-N CC1=C(C=CC=C1C)N(C#N)S(=O)(=O)C1=CC=C(C)C=C1 Chemical compound CC1=C(C=CC=C1C)N(C#N)S(=O)(=O)C1=CC=C(C)C=C1 IGPHOCUPTPJKQY-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical compound CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002542 isoureas Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- JMSCRSRHQXBZSD-UHFFFAOYSA-N sulfonylcyanamide Chemical class O=S(=O)=NC#N JMSCRSRHQXBZSD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/55—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/58—Y being a hetero atom
- C07C275/60—Y being an oxygen atom, e.g. allophanic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7340527A FR2271202A1 (en) | 1973-11-14 | 1973-11-14 | Substituted ureas, acylureas and sulphonylureas prodn - by reacting a substituted cyanamide with a cpd forming a carbonium ion |
| FR7435907A FR2288735A2 (fr) | 1974-10-25 | 1974-10-25 | Derives de l'uree, acylurees et sulfonylurees substituees et leur procede de fabrication |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2454107A1 DE2454107A1 (de) | 1975-05-22 |
| DE2454107B2 true DE2454107B2 (de) | 1977-01-13 |
Family
ID=26218025
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742454107 Granted DE2454107B2 (de) | 1973-11-14 | 1974-11-14 | Verfahren zur herstellung von harnstoffen, acylharnstoffen und sulfonylharnstoffen |
| DE2462011A Expired DE2462011C3 (de) | 1973-11-14 | 1974-11-14 | Cyanamide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2462011A Expired DE2462011C3 (de) | 1973-11-14 | 1974-11-14 | Cyanamide |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4013706A (enExample) |
| JP (1) | JPS5831341B2 (enExample) |
| CH (1) | CH605700A5 (enExample) |
| DE (2) | DE2454107B2 (enExample) |
| GB (2) | GB1476797A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6033109B2 (ja) * | 1977-04-28 | 1985-08-01 | 塩野義製薬株式会社 | 尿素誘導体の合成法 |
| DE2733181B2 (de) * | 1977-07-22 | 1979-08-30 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von N-substituierten a -Ketocarbonsäureamiden |
| DE2919292A1 (de) * | 1979-05-12 | 1980-11-20 | Bayer Ag | Substituierte harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als pflanzenbakterizide |
| DE2934248A1 (de) | 1979-08-24 | 1981-03-26 | Hoechst Ag, 65929 Frankfurt | Wasserloesliche phthalocyaninverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| DE2934247A1 (de) * | 1979-08-24 | 1981-04-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur veredlung von faserigen materialien |
| US4399152A (en) * | 1980-04-03 | 1983-08-16 | Duphar International B.V. | Substituted benzoyl ureas as insecticides |
| DE3035393A1 (de) * | 1980-09-19 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung vonn-substituierten imidodicarbonsaeurediarylestern |
| US4618712A (en) * | 1982-02-23 | 1986-10-21 | Ciba-Geigy Corporation | N-cyanocarboxylic acid amides, processes for their preparation and their use |
| GB2226815A (en) * | 1989-01-06 | 1990-07-11 | Shell Int Research | Fungicidal n-acyl cyanamides |
| US5254589A (en) * | 1991-10-15 | 1993-10-19 | Warner-Lambert Company | Sulfonyl urea and carbamate ACAT inhibitors |
| HU228303B1 (hu) * | 1999-07-13 | 2013-03-28 | Lonza Ag | Eljárás 2-amino-4-(4-fluorfenil)-6-alkil-pirimidin-5-karboxilát-származékok elõállítására |
| CN106008260A (zh) * | 2016-06-08 | 2016-10-12 | 刘利楠 | 一种芳氰基化合物的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427323A (en) * | 1964-07-16 | 1969-02-11 | Du Pont | Alpha-alkoxyalkylcyanamides and their preparation |
| US3332994A (en) * | 1966-06-17 | 1967-07-25 | Du Pont | Alkoxycyanamides and their preparation |
| NL160809C (nl) * | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
-
1974
- 1974-11-13 US US05/523,550 patent/US4013706A/en not_active Expired - Lifetime
- 1974-11-14 DE DE19742454107 patent/DE2454107B2/de active Granted
- 1974-11-14 GB GB4967875A patent/GB1476797A/en not_active Expired
- 1974-11-14 CH CH1520374A patent/CH605700A5/xx not_active IP Right Cessation
- 1974-11-14 JP JP49131845A patent/JPS5831341B2/ja not_active Expired
- 1974-11-14 DE DE2462011A patent/DE2462011C3/de not_active Expired
- 1974-11-14 GB GB4931974A patent/GB1476796A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2454107A1 (de) | 1975-05-22 |
| CH605700A5 (enExample) | 1978-10-13 |
| JPS5831341B2 (ja) | 1983-07-05 |
| JPS5083331A (enExample) | 1975-07-05 |
| DE2462011C3 (de) | 1978-05-03 |
| US4013706A (en) | 1977-03-22 |
| DE2462011A1 (de) | 1975-06-26 |
| DE2462011B2 (de) | 1977-09-22 |
| GB1476797A (en) | 1977-06-16 |
| GB1476796A (en) | 1977-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |