CA2336657C - Method for producing carbonyl diimidazoles - Google Patents
Method for producing carbonyl diimidazoles Download PDFInfo
- Publication number
- CA2336657C CA2336657C CA002336657A CA2336657A CA2336657C CA 2336657 C CA2336657 C CA 2336657C CA 002336657 A CA002336657 A CA 002336657A CA 2336657 A CA2336657 A CA 2336657A CA 2336657 C CA2336657 C CA 2336657C
- Authority
- CA
- Canada
- Prior art keywords
- imidazole
- nitrogen base
- base
- radicals
- reaction mixture
- 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.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- GRSTVVGJSKHCCS-UHFFFAOYSA-N bis(1h-imidazol-2-yl)methanone Chemical class N=1C=CNC=1C(=O)C1=NC=CN1 GRSTVVGJSKHCCS-UHFFFAOYSA-N 0.000 title abstract 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000011541 reaction mixture Substances 0.000 claims abstract description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 C1-C4 alkyl radical Chemical group 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 5
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 28
- 239000002585 base Substances 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 5
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000008096 xylene Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19830556.7 | 1998-07-08 | ||
| DE19830556A DE19830556A1 (de) | 1998-07-08 | 1998-07-08 | Verfahren zur Herstellung von Carbonyldiimidazolen |
| PCT/EP1999/004729 WO2000002863A1 (de) | 1998-07-08 | 1999-07-06 | Verfahren zur herstellung von carbonyldiimidazolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2336657A1 CA2336657A1 (en) | 2000-01-20 |
| CA2336657C true CA2336657C (en) | 2009-02-24 |
Family
ID=7873373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002336657A Expired - Fee Related CA2336657C (en) | 1998-07-08 | 1999-07-06 | Method for producing carbonyl diimidazoles |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6353115B1 (https=) |
| EP (1) | EP1095024B1 (https=) |
| JP (1) | JP2002520318A (https=) |
| KR (1) | KR20010071762A (https=) |
| CN (1) | CN1214012C (https=) |
| AU (1) | AU5409899A (https=) |
| CA (1) | CA2336657C (https=) |
| DE (2) | DE19830556A1 (https=) |
| HU (1) | HUP0102739A3 (https=) |
| WO (1) | WO2000002863A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10359797A1 (de) * | 2003-12-19 | 2005-07-21 | Bayer Chemicals Ag | Verfahren zur Herstellung von N,N'-Carbonyldiazolen |
| EP1731510B1 (en) * | 2004-03-30 | 2015-07-29 | Hodogaya Chemical Co., Ltd. | Process for producing n,n'-carbonyldiimidazole |
| CN102321026A (zh) * | 2011-08-02 | 2012-01-18 | 海门瑞一医药科技有限公司 | 羰基二咪唑的生产工艺 |
| KR102473775B1 (ko) * | 2022-04-15 | 2022-12-05 | ㈜파인켐 | 카르밤산염 유도체 화합물 제조방법 |
| CN120398768B (zh) * | 2025-04-30 | 2025-10-17 | 江西金凯化工有限公司 | 一种利用固体三光气的n,n'-羰基二咪唑高纯度制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4118585B1 (https=) * | 1963-11-04 | 1966-10-26 | ||
| GB1408877A (en) * | 1971-12-07 | 1975-10-08 | Boots Co Ltd | Substituted imidazoles and their use as pesticides |
| GB1469772A (en) | 1973-06-21 | 1977-04-06 | Boots Co Ltd | Fungicidal imidazole derivatives |
| JPS5816639A (ja) * | 1981-04-23 | 1983-01-31 | ザ・プロクタ−・エンド・ギヤンブル・カンパニ− | 塩、レシチン及び親水性シリカを含有する脂肪組成物 |
| DE3134933A1 (de) * | 1981-09-03 | 1983-03-31 | Hoechst Ag, 6230 Frankfurt | "harnstoffderivate, verfahren zu ihrer herstellung und diese enthaltende medikamente sowie deren verwendung" |
| JPS58152863A (ja) * | 1982-03-04 | 1983-09-10 | Sumitomo Chem Co Ltd | カルボニルジイミノビスベンゼンスルホニルクロリド類の製造方法 |
| US4957933A (en) * | 1989-04-21 | 1990-09-18 | E. I. Du Pont De Nemours And Company | Fungicidal oxazolidinones |
| US5270317A (en) * | 1990-03-20 | 1993-12-14 | Elf Sanofi | N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions in which they are present |
| JP3021705B2 (ja) * | 1991-03-01 | 2000-03-15 | 住友化学工業株式会社 | 対称型１，３−ジ置換尿素の製造法 |
| BR9307577A (pt) * | 1992-11-13 | 1999-05-25 | Du Pont | Processo para preparação de 2,4-oxazolidinadionas e intermediário |
| DE4424400A1 (de) | 1994-07-11 | 1996-01-18 | Bayer Ag | Verbessertes Verfahren zur Herstellung von N,N'-Carbonyldiazolen, insbesondere N,N'-Carbonyldiimidazol |
| JPH08253456A (ja) * | 1995-03-17 | 1996-10-01 | Mitsubishi Chem Corp | ２−ペルヒドロピリミジノン誘導体及びそれを有効成分とする除草剤、並びにその製造中間体 |
| EP1019381A1 (en) * | 1997-01-17 | 2000-07-19 | Ppg Industries, Inc. | Method of producing n,n'-diazole compounds |
| DE19833913A1 (de) * | 1998-07-28 | 2000-02-03 | Bayer Ag | Verfahren zur Herstellung von N,N'-Carbonyldiazolen |
-
1998
- 1998-07-08 DE DE19830556A patent/DE19830556A1/de not_active Withdrawn
-
1999
- 1999-07-06 HU HU0102739A patent/HUP0102739A3/hu unknown
- 1999-07-06 AU AU54098/99A patent/AU5409899A/en not_active Abandoned
- 1999-07-06 EP EP99939989A patent/EP1095024B1/de not_active Expired - Lifetime
- 1999-07-06 US US09/720,913 patent/US6353115B1/en not_active Expired - Fee Related
- 1999-07-06 JP JP2000559094A patent/JP2002520318A/ja active Pending
- 1999-07-06 CN CNB998083860A patent/CN1214012C/zh not_active Expired - Fee Related
- 1999-07-06 DE DE59907811T patent/DE59907811D1/de not_active Expired - Fee Related
- 1999-07-06 KR KR1020017000204A patent/KR20010071762A/ko not_active Withdrawn
- 1999-07-06 CA CA002336657A patent/CA2336657C/en not_active Expired - Fee Related
- 1999-07-06 WO PCT/EP1999/004729 patent/WO2000002863A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE59907811D1 (de) | 2003-12-24 |
| EP1095024A1 (de) | 2001-05-02 |
| AU5409899A (en) | 2000-02-01 |
| EP1095024B1 (de) | 2003-11-19 |
| CN1308613A (zh) | 2001-08-15 |
| US6353115B1 (en) | 2002-03-05 |
| HUP0102739A2 (hu) | 2001-11-28 |
| WO2000002863A1 (de) | 2000-01-20 |
| HUP0102739A3 (en) | 2003-03-28 |
| CN1214012C (zh) | 2005-08-10 |
| KR20010071762A (ko) | 2001-07-31 |
| JP2002520318A (ja) | 2002-07-09 |
| DE19830556A1 (de) | 2000-01-13 |
| CA2336657A1 (en) | 2000-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |