WO1992019600A1 - Preparation of n-acylimidazoles - Google Patents
Preparation of n-acylimidazoles Download PDFInfo
- Publication number
- WO1992019600A1 WO1992019600A1 PCT/US1992/003322 US9203322W WO9219600A1 WO 1992019600 A1 WO1992019600 A1 WO 1992019600A1 US 9203322 W US9203322 W US 9203322W WO 9219600 A1 WO9219600 A1 WO 9219600A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- anhydride
- recited
- carbonyldiimidazole
- carboxylic
- groups
- Prior art date
Links
Classifications
-
- 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
-
- 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
Definitions
- N-acylimidazoles which gives only easily removable CO 2 as a byproduct, and fully utilizes all of the imidazole groups in the carbonyldiimidazole (all of the imidazole groups become N-acylimidazole).
- This invention concerns a process for the
- N-acylimidazoles comprising, contacting a carboxylic anhydride with a carbonyldiimidazole.
- This invention concerns the production of
- N-acylimidazoles by the reaction of a carboxylic acid
- the carbonyldiimidazole has the formula
- the imidazole rings of the carbonyldimidazole may be substituted in the 2, 4 or 5 position. It is preferred that in the carbonyldiimidazole both imidazole rings are unsubstituted, that is the compound 1,1'-carbonyldimidazole.
- N-acylimidazole is meant a compound of the type
- an acyl group is bound to the 1 position of an imidazole ring.
- the group R 1 is hydrocarbyl, which may be substituted with various substituents.
- the various substituents on the imidazole ring or attached to the group R 1 should be inert under process conditions.
- the group R 1 is derived from the carboxylic
- Carboxylic anhydrides are well known to those skilled in the art and contain the group -C(O)-O-C(O)-, where the free bonds are to hydrocarbyl or substituted hydrocarbyl groups, such as the group R 1 .
- Carboxylic anhydrides may be cyclic or acyclic.
- the carboxylic anhydride may have the formula R 1 C(O)-O-C(O)R 1 , wherein each R 1 is independently hydrocarbyl, or both hydrocarbyl groups R 1 may be joined to each other to form a cyclic anhydride.
- acyclic carboxylic anhydrides useful in the instant process are acetic anhydride, perfluorobutyric anhydride, trifluoroacetic anhydride, benzoic anhydride, hexanoic anhydride, and methacrylic anhydride. These acyclic anhydrides may also be so-called mixed
- anhydrides such as acetic propanoic anhydride.
- mixed anhydrides two N-acylimidazoles will be obtained, each derived from one of the acyl groups in the mixed anhydride.
- Symmetrical anhydrides both R 1 groups the same are preferred.
- a typical reaction of a CDI with an acyclic carboxylic anhydride is:
- Cyclic anhydrides are also useful in the instant process.
- examples of such cyclic anhydrides include, but are not limited to, succinic anhydride, maleic anhydride, phthalic anhydride, and itaconic anhydride.
- a cyclic anhydride reacts with a CDI a compound containing two N-acylimidazole groups will be produced (assuming only one anhydride group per cyclic anhydride molecule), since the anhydride groups are also connected by the cyclic structure.
- reaction of phthalic anhydride with a CDI proceeds as follows:
- substituents that may be present either in the carboxylic anhydride (for example, the group R 1 ) or in the 2, 4 or 5 positions of the imidazole ring of the CDI (and hence also present in the N-acylimidazole product), include, but are not limited to ether, ester, amide, fluoro, chloro, bromo, and iodo, and for substitution in the imidazole ring, hydrocarbyl. Any combination of substituents in any of these
- the carboxylic anhydride may be part of a much larger molecule, such as a polymer.
- the carboxylic anhydride may be maleic anhydride or itaconic anhydride that has been (usually free radically)
- the carboxylic anhydride may also contain more than one anhydride group, as in
- anhydride groups in the copolymer are cyclic.
- the ratio of total anhydride groups to the CDI is about 1. This insures the most efficient use of the starting materials, and obviates the need for removal of
- solvents is optional, and any solvent used should be aprotic. Solvents are particularly useful when the ingredients are not miscible or one or both of the ingredients are solid at the process temperature.
- a useful solvent is methylene chloride.
- Useful solvent types include halocarbons, esters, aromatics, etc.
- Protic solvents such as alcohols, water, primary and secondary amines should be avoided.
- the product N-acylimidazole may be used directly as made in the process, since the only byproduct is gaseous CO 2 . If a solvent is used, it may be removed by
- N-acylimidazole may be purified by distillation or crystallization, as
- N-acylimidazoles are useful intermediates for the preparation esters, amides, peptides, carboxylic anhydrides, and other types of organic compounds. This reference also describes the preparation of CDIs.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69213447T DE69213447T2 (en) | 1988-12-15 | 1992-04-29 | PRODUCTION OF N-ACYLIMIDAZOLES |
EP92911954A EP0583375B1 (en) | 1988-12-15 | 1992-04-29 | Preparation of n-acylimidazoles |
JP4511895A JPH06507411A (en) | 1988-12-15 | 1992-04-29 | Production of N-acylimidazole |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/284,896 US5084280A (en) | 1988-12-15 | 1988-12-15 | Wood preservation composition and method |
US695,157 | 1991-05-03 | ||
US07/695,157 US5145983A (en) | 1988-12-15 | 1991-05-03 | Preparation of N-acylimidazoles |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992019600A1 true WO1992019600A1 (en) | 1992-11-12 |
Family
ID=40290953
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1992/003322 WO1992019600A1 (en) | 1988-12-15 | 1992-04-29 | Preparation of n-acylimidazoles |
Country Status (6)
Country | Link |
---|---|
US (2) | US5084280A (en) |
EP (2) | EP0539619A1 (en) |
JP (1) | JPH06507411A (en) |
CA (2) | CA2004637C (en) |
DE (2) | DE4126986A1 (en) |
WO (1) | WO1992019600A1 (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5084280A (en) * | 1988-12-15 | 1992-01-28 | Chapman Chemical Company | Wood preservation composition and method |
US5470986A (en) * | 1994-06-27 | 1995-11-28 | E. I. Du Pont De Nemours And Company | Imidazolium hardeners for hydrophilic colloid |
US5846305A (en) * | 1996-01-16 | 1998-12-08 | Michael Wall & Sons Enterprises Ltd. | Liquid wood preservative solution |
DE19614799A1 (en) * | 1996-04-15 | 1997-10-16 | Ostermann & Scheiwe Gmbh & Co | Process for the protection of laminated glulam and glulam from rot |
DE19724884A1 (en) * | 1997-06-12 | 1998-12-17 | Basf Ag | Carbonyldiimidazoles, esters derived therefrom and processes for their preparation |
SI1255752T1 (en) * | 2000-02-15 | 2007-12-31 | Pharmacia & Upjohn Co Llc | Pyrrole substituted 2-indolinone protein kinase inhibitors |
AR042586A1 (en) | 2001-02-15 | 2005-06-29 | Sugen Inc | 3- (4-AMIDOPIRROL-2-ILMETILIDEN) -2-INDOLINONE AS INHIBITORS OF PROTEIN KINASE; YOUR PHARMACEUTICAL COMPOSITIONS; A METHOD FOR THE MODULATION OF THE CATALYTIC ACTIVITY OF PROTEINQUINASE; A METHOD TO TREAT OR PREVENT AN AFFECTION RELATED TO PROTEINQUINASE |
CA2357357C (en) | 2001-09-17 | 2010-03-16 | Genics Inc. | Method of treating building materials with boron and building materials |
EP1434774A1 (en) | 2001-10-10 | 2004-07-07 | Sugen, Inc. | 3-(4-substituted heterocyclyl)-pyrrol-2-ylmethylidene)-2-indolinone derivatives as protein kinase inhibitors |
GB0700857D0 (en) * | 2007-01-17 | 2007-02-21 | Betts John A | Preservative compositions for wood and like materials |
US8221797B2 (en) * | 2007-02-09 | 2012-07-17 | Osmose, Inc. | Wood preserving composition for treatment of in-service poles, posts, piling, cross-ties and other wooded structures |
CN102633725A (en) * | 2012-04-10 | 2012-08-15 | 浏阳坛青达康医药科技有限公司 | Synthetic method of N-heptafluorobutyrylimidazole |
US9303169B2 (en) | 2014-06-16 | 2016-04-05 | Osmose Utilities Services, Inc. | Controlled release, wood preserving composition with low-volatile organic content for treatment in-service utility poles, posts, pilings, cross-ties and other wooden structures |
CN110568104A (en) * | 2019-09-24 | 2019-12-13 | 杭州市质量技术监督检测院 | Method for simultaneously measuring migration volumes of various chlorinated phenols in wooden tableware |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2703023A1 (en) * | 1977-01-26 | 1978-07-27 | Basf Ag | FURANDERIVATE |
CA1174004A (en) * | 1982-09-28 | 1984-09-11 | John Krzyzewski | Arsenical creosote wood preservative |
US5084280A (en) * | 1988-12-15 | 1992-01-28 | Chapman Chemical Company | Wood preservation composition and method |
-
1988
- 1988-12-15 US US07/284,896 patent/US5084280A/en not_active Expired - Lifetime
-
1989
- 1989-12-05 CA CA002004637A patent/CA2004637C/en not_active Expired - Lifetime
-
1991
- 1991-05-03 US US07/695,157 patent/US5145983A/en not_active Expired - Lifetime
- 1991-08-15 DE DE4126986A patent/DE4126986A1/en not_active Withdrawn
- 1991-10-31 EP EP91118593A patent/EP0539619A1/en not_active Withdrawn
-
1992
- 1992-04-29 JP JP4511895A patent/JPH06507411A/en active Pending
- 1992-04-29 DE DE69213447T patent/DE69213447T2/en not_active Expired - Fee Related
- 1992-04-29 CA CA002109229A patent/CA2109229A1/en not_active Abandoned
- 1992-04-29 EP EP92911954A patent/EP0583375B1/en not_active Expired - Lifetime
- 1992-04-29 WO PCT/US1992/003322 patent/WO1992019600A1/en active IP Right Grant
Non-Patent Citations (3)
Title |
---|
ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. vol. 1, 1962, WEINHEIM DE pages 351 - 367; cited in the application * |
SYNTHESIS. vol. 10, 1990, STUTTGART DE pages 951 - 955; * |
TETRAHEDRON, (INCL. TETRAHEDRON REPORTS) vol. 36, no. 17, 1980, OXFORD GB pages 2505 - 2511; * |
Also Published As
Publication number | Publication date |
---|---|
CA2004637A1 (en) | 1990-06-15 |
JPH06507411A (en) | 1994-08-25 |
DE4126986A1 (en) | 1993-02-18 |
DE69213447D1 (en) | 1996-10-10 |
EP0539619A1 (en) | 1993-05-05 |
US5084280A (en) | 1992-01-28 |
DE69213447T2 (en) | 1997-02-20 |
US5145983A (en) | 1992-09-08 |
EP0583375B1 (en) | 1996-09-04 |
EP0583375A1 (en) | 1994-02-23 |
CA2004637C (en) | 1996-12-24 |
CA2109229A1 (en) | 1992-11-04 |
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