JP2002520318A - カルボニルジイミダゾールの製造方法 - Google Patents
カルボニルジイミダゾールの製造方法Info
- Publication number
- JP2002520318A JP2002520318A JP2000559094A JP2000559094A JP2002520318A JP 2002520318 A JP2002520318 A JP 2002520318A JP 2000559094 A JP2000559094 A JP 2000559094A JP 2000559094 A JP2000559094 A JP 2000559094A JP 2002520318 A JP2002520318 A JP 2002520318A
- Authority
- JP
- Japan
- Prior art keywords
- imidazole
- xylene
- base
- solvent
- nitrogen
- 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
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 93
- 238000000034 method Methods 0.000 claims abstract description 30
- 239000011541 reaction mixture Substances 0.000 claims abstract description 15
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
- 239000012442 inert solvent Substances 0.000 claims abstract description 5
- 125000001477 organic nitrogen group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000002585 base Substances 0.000 claims description 24
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000008096 xylene Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 8
- 238000003786 synthesis reaction Methods 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
- 239000003960 organic solvent Substances 0.000 claims description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group 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
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 amine hydrochloride Chemical class 0.000 description 4
- 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
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001035 drying Methods 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
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent 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
- 238000010992 reflux Methods 0.000 description 2
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 2
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-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
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013877 carbamide Nutrition 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
- 238000005119 centrifugation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000005259 measurement Methods 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
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000013519 translation 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 |
|---|---|
| JP2002520318A true JP2002520318A (ja) | 2002-07-09 |
| JP2002520318A5 JP2002520318A5 (https=) | 2006-06-15 |
Family
ID=7873373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000559094A Pending JP2002520318A (ja) | 1998-07-08 | 1999-07-06 | カルボニルジイミダゾールの製造方法 |
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=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4846568B2 (ja) * | 2004-03-30 | 2011-12-28 | 保土谷化学工業株式会社 | Ｎ，ｎ’−カルボニルジイミダゾールの製造方法 |
Families Citing this family (4)
| 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 |
| 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 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4118585B1 (https=) * | 1963-11-04 | 1966-10-26 | ||
| JPS57209267A (en) * | 1981-05-20 | 1982-12-22 | Robins Co Inc A H | N-(arylthioalkyl)-n'-(aminoalkyl)urea and antiarrhyhmic |
| JPS5855451A (ja) * | 1981-09-03 | 1983-04-01 | ヘキスト・アクチエンゲゼルシヤフト | 尿素誘導体およびその製法 |
| 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 |
| JPH04273850A (ja) * | 1991-03-01 | 1992-09-30 | Sumitomo Chem Co Ltd | 対称型１，３−ジ置換尿素の製造法 |
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4118585B1 (https=) * | 1963-11-04 | 1966-10-26 | ||
| JPS57209267A (en) * | 1981-05-20 | 1982-12-22 | Robins Co Inc A H | N-(arylthioalkyl)-n'-(aminoalkyl)urea and antiarrhyhmic |
| JPS5855451A (ja) * | 1981-09-03 | 1983-04-01 | ヘキスト・アクチエンゲゼルシヤフト | 尿素誘導体およびその製法 |
| 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 |
| JPH04273850A (ja) * | 1991-03-01 | 1992-09-30 | Sumitomo Chem Co Ltd | 対称型１，３−ジ置換尿素の製造法 |
| 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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4846568B2 (ja) * | 2004-03-30 | 2011-12-28 | 保土谷化学工業株式会社 | Ｎ，ｎ’−カルボニルジイミダゾールの製造方法 |
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 |
| CA2336657C (en) | 2009-02-24 |
| 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 |
| DE19830556A1 (de) | 2000-01-13 |
| CA2336657A1 (en) | 2000-01-20 |
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