CA1058621A - Process for the preparation of 5-acetoacetylamino benzimidazolone - Google Patents
Process for the preparation of 5-acetoacetylamino benzimidazoloneInfo
- Publication number
- CA1058621A CA1058621A CA251,369A CA251369A CA1058621A CA 1058621 A CA1058621 A CA 1058621A CA 251369 A CA251369 A CA 251369A CA 1058621 A CA1058621 A CA 1058621A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- acid
- benzimidazolone
- acetoacetylamino
- added
- 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
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims 2
- KQNZKBRSEJLVEO-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-5-yl)butanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=CC2=NC(=O)N=C21 KQNZKBRSEJLVEO-UHFFFAOYSA-N 0.000 title 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 6
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 4
- 239000003638 chemical reducing agent Substances 0.000 claims abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- CSABAZBYIWDIDE-UHFFFAOYSA-N sulfino hydrogen sulfite Chemical class OS(=O)OS(O)=O CSABAZBYIWDIDE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 229940079826 hydrogen sulfite Drugs 0.000 claims 1
- 229960004838 phosphoric acid Drugs 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- -1 alkali metal sulfites Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QOMNJPSRBRDQSU-UHFFFAOYSA-N 5-aminobenzimidazol-2-one Chemical compound C1=C(N)C=CC2=NC(=O)N=C21 QOMNJPSRBRDQSU-UHFFFAOYSA-N 0.000 description 1
- CLHXKSVLPCOPHR-UHFFFAOYSA-N 5-nitrobenzimidazol-2-one Chemical compound C1=C([N+](=O)[O-])C=CC2=NC(=O)N=C21 CLHXKSVLPCOPHR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008395 clarifying agent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2518922A DE2518922C2 (de) | 1975-04-29 | 1975-04-29 | Verfahren zur Herstellung von 5- Acetoacetylaminobenzimidazolon-(2) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058621A true CA1058621A (en) | 1979-07-17 |
Family
ID=5945233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,369A Expired CA1058621A (en) | 1975-04-29 | 1976-04-28 | Process for the preparation of 5-acetoacetylamino benzimidazolone |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4087610A (enExample) |
| JP (1) | JPS5910664B2 (enExample) |
| BE (1) | BE841284A (enExample) |
| CA (1) | CA1058621A (enExample) |
| CH (1) | CH603597A5 (enExample) |
| DE (1) | DE2518922C2 (enExample) |
| FR (1) | FR2309542A1 (enExample) |
| GB (1) | GB1534077A (enExample) |
| IN (1) | IN144220B (enExample) |
| IT (1) | IT1062997B (enExample) |
| NL (1) | NL7604355A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2612391C2 (de) * | 1976-03-24 | 1982-09-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-(2) |
| DE4335614A1 (de) * | 1993-10-19 | 1995-04-27 | Hoechst Ag | Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-2 |
| CN104130193B (zh) * | 2014-08-12 | 2016-09-28 | 南通醋酸化工股份有限公司 | 一种5-乙酰乙酰氨基苯并咪唑酮的合成方法 |
| CN108101850B (zh) * | 2017-12-21 | 2021-12-07 | 山东汇海医药化工有限公司 | 一种提高5-乙酰乙酰氨基苯并咪唑酮质量的方法 |
| CN109748877A (zh) * | 2019-03-21 | 2019-05-14 | 济南大学 | 一种5-乙酰乙酰氨基苯并咪唑酮的制备方法 |
| CN110128350A (zh) * | 2019-07-01 | 2019-08-16 | 山东汇海医药化工有限公司 | 一种提高5-乙酰乙酰氨基苯并咪唑酮质量的方法 |
| CN110845424B (zh) * | 2019-12-11 | 2021-03-26 | 山东汇海医药化工有限公司 | 一种5-乙酰乙酰氨基苯并咪唑酮的制备方法 |
| CN111039872A (zh) * | 2019-12-11 | 2020-04-21 | 山东汇海医药化工有限公司 | 一种提高5-乙酰乙酰氨基苯并咪唑酮收率的方法 |
| CN111763174B (zh) * | 2020-08-03 | 2023-06-09 | 山东汇海医药化工有限公司 | 一种减少5-乙酰乙酰氨基苯并咪唑酮母液蒸馏残渣的方法 |
| CN114369066A (zh) * | 2021-12-09 | 2022-04-19 | 山东汇海医药化工有限公司 | 一种5-乙酰乙酰氨基苯并咪唑酮母液循环利用的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1982675A (en) * | 1934-12-04 | Pbeparation of acetoacetanilid | ||
| US2152132A (en) * | 1936-12-12 | 1939-03-28 | Carbide & Carbon Chem Corp | Acetoacetyl amides and process for their preparation |
| BE513633A (enExample) * | 1951-08-21 | |||
| GB770263A (en) * | 1954-06-19 | 1957-03-20 | Wacker Chemie Gmbh | Process for the manufacture of acetoacetamides |
| GB962227A (en) * | 1960-08-23 | 1964-07-01 | Distillers Co Yeast Ltd | Production of aceto-acetarylamides |
| BE622476A (enExample) * | 1961-09-14 | |||
| DE1644231A1 (de) * | 1967-10-27 | 1970-12-10 | Hoechst Ag | Wasserunloeslicher Monoazofarbstoff und Verfahren zu seiner Herstellung |
| US3963694A (en) * | 1971-03-03 | 1976-06-15 | Ciba-Geigy Corporation | Hydroxyquinolyl- and quinazolonylazoacetoacetylbenzimidazolone pigments |
-
1975
- 1975-04-29 DE DE2518922A patent/DE2518922C2/de not_active Expired
-
1976
- 1976-04-23 NL NL7604355A patent/NL7604355A/xx not_active Application Discontinuation
- 1976-04-23 CH CH515476A patent/CH603597A5/xx not_active IP Right Cessation
- 1976-04-27 IN IN735/CAL/1976A patent/IN144220B/en unknown
- 1976-04-27 IT IT22738/76A patent/IT1062997B/it active
- 1976-04-27 US US05/680,719 patent/US4087610A/en not_active Expired - Lifetime
- 1976-04-28 JP JP51047929A patent/JPS5910664B2/ja not_active Expired
- 1976-04-28 CA CA251,369A patent/CA1058621A/en not_active Expired
- 1976-04-29 GB GB17484/76A patent/GB1534077A/en not_active Expired
- 1976-04-29 FR FR7612714A patent/FR2309542A1/fr active Granted
- 1976-04-29 BE BE166575A patent/BE841284A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7604355A (nl) | 1976-11-02 |
| IT1062997B (it) | 1985-02-11 |
| DE2518922A1 (de) | 1976-11-18 |
| DE2518922C2 (de) | 1982-08-19 |
| FR2309542A1 (fr) | 1976-11-26 |
| CH603597A5 (enExample) | 1978-08-31 |
| JPS51131876A (en) | 1976-11-16 |
| BE841284A (fr) | 1976-10-29 |
| JPS5910664B2 (ja) | 1984-03-10 |
| FR2309542B1 (enExample) | 1980-08-01 |
| US4087610A (en) | 1978-05-02 |
| IN144220B (enExample) | 1978-04-08 |
| GB1534077A (en) | 1978-11-29 |
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