WO1998031672B1 - Procede d'elaboration de composes n, n'-diazole - Google Patents
Procede d'elaboration de composes n, n'-diazoleInfo
- Publication number
- WO1998031672B1 WO1998031672B1 PCT/US1998/000592 US9800592W WO9831672B1 WO 1998031672 B1 WO1998031672 B1 WO 1998031672B1 US 9800592 W US9800592 W US 9800592W WO 9831672 B1 WO9831672 B1 WO 9831672B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- unsubstituted
- compound
- inert solvent
- molar ratio
- tertiary amine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 18
- 239000012442 inert solvent Substances 0.000 claims abstract 15
- 150000003512 tertiary amines Chemical class 0.000 claims abstract 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
- -1 e.g. Substances 0.000 claims abstract 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract 7
- 150000007530 organic bases Chemical class 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 7
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims abstract 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 4
- 239000003849 aromatic solvent Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- AVDNGGJZZVTQNA-UHFFFAOYSA-N di(pyrrol-1-yl)methanone Chemical compound C1=CC=CN1C(=O)N1C=CC=C1 AVDNGGJZZVTQNA-UHFFFAOYSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- DQRZHDZZXRUAEB-UHFFFAOYSA-N 1-pyrrol-1-ylsulfinylpyrrole Chemical class C1=CC=CN1S(=O)N1C=CC=C1 DQRZHDZZXRUAEB-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229940086542 triethylamine Drugs 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract 2
Abstract
Procédé d'élaboration de composés N, N'-diazole, par exemple N, N'-carbonyldiimidazole, consistant à établir la réaction dans un solvant inerte, par exemple toluène, d'un composé 1H-azole 1-non substitué, par exemple 1H-imidazole, et d'un composé dihaloïde, par exemple phosgène, en présence d'une base organique, par exemple amine tertiaire du type tri(n-butyl)amine. Le rapport molaire entre le composé 1H-azole non substitué en 1 et le composé dihaloïde peut aller de 1,7: 1 à 2,3: 1. Le rapport molaire entre la base organique et le composé 1H-azole non substitué en 1 est 1: 1 lorsque le rapport molaire entre le composé 1H-azole non substitué en 1 et le composé dihaloïde est inférieur à 2: 1. La base organique a une basicité supérieure à celle du composé 1H-azole non substitué en 1, et elle est soluble dans le solvant inerte avec son sel d'hydrohaloïde.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002278179A CA2278179A1 (fr) | 1997-01-17 | 1998-01-09 | Procede d'elaboration de composes n, n'-diazole |
| EP98901791A EP1019381A1 (fr) | 1997-01-17 | 1998-01-09 | Procede d'elaboration de composes n, n'-diazole |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78562697A | 1997-01-17 | 1997-01-17 | |
| US08/785,626 | 1997-01-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998031672A1 WO1998031672A1 (fr) | 1998-07-23 |
| WO1998031672B1 true WO1998031672B1 (fr) | 1998-09-03 |
Family
ID=25136102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1998/000592 WO1998031672A1 (fr) | 1997-01-17 | 1998-01-09 | Procede d'elaboration de composes n, n'-diazole |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1019381A1 (fr) |
| CN (1) | CN1109021C (fr) |
| CA (1) | CA2278179A1 (fr) |
| WO (1) | WO1998031672A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19830556A1 (de) | 1998-07-08 | 2000-01-13 | Basf Ag | Verfahren zur Herstellung von Carbonyldiimidazolen |
| DE19833913A1 (de) | 1998-07-28 | 2000-02-03 | Bayer Ag | Verfahren zur Herstellung von N,N'-Carbonyldiazolen |
| DE10035011A1 (de) * | 2000-07-19 | 2002-01-31 | Bayer Ag | Verfahren zur Herstellung von N,N`-Carbonyldiazolen und Azolidsalzen |
| US6455702B1 (en) * | 2001-05-16 | 2002-09-24 | Aims Fine Chemicals, Inc. | Process for the production of N,N-carbonyl diimidazole |
| 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 |
| CN104496908A (zh) * | 2014-12-24 | 2015-04-08 | 江苏康乐新材料科技有限公司 | 一种羰基二咪唑的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1469772A (en) * | 1973-06-21 | 1977-04-06 | Boots Co Ltd | Fungicidal imidazole derivatives |
| US3997071A (en) * | 1975-08-14 | 1976-12-14 | Laserplane Corporation | Method and apparatus for indicating effective digging depth of a backhoe |
| ATE149157T1 (de) * | 1992-11-13 | 1997-03-15 | Du Pont | Verfahren zur herstellung von 2,4- oxazolidinedionen |
-
1998
- 1998-01-09 CA CA002278179A patent/CA2278179A1/fr not_active Abandoned
- 1998-01-09 EP EP98901791A patent/EP1019381A1/fr not_active Withdrawn
- 1998-01-09 WO PCT/US1998/000592 patent/WO1998031672A1/fr active Application Filing
- 1998-01-09 CN CN98802686A patent/CN1109021C/zh not_active Expired - Fee Related
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