DE2518922C2 - Verfahren zur Herstellung von 5- Acetoacetylaminobenzimidazolon-(2) - Google Patents
Verfahren zur Herstellung von 5- Acetoacetylaminobenzimidazolon-(2)Info
- Publication number
- DE2518922C2 DE2518922C2 DE2518922A DE2518922A DE2518922C2 DE 2518922 C2 DE2518922 C2 DE 2518922C2 DE 2518922 A DE2518922 A DE 2518922A DE 2518922 A DE2518922 A DE 2518922A DE 2518922 C2 DE2518922 C2 DE 2518922C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- alkali metal
- diketene
- salt
- aminobenzimidazolone
- 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 9
- 238000002360 preparation method Methods 0.000 title claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 13
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 10
- -1 5-amino-5-aminobenzimidazolone Chemical compound 0.000 claims description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- KQNZKBRSEJLVEO-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-5-yl)butanamide Chemical class C1=C(NC(=O)CC(=O)C)C=CC2=NC(=O)N=C21 KQNZKBRSEJLVEO-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229940079827 sodium hydrogen sulfite Drugs 0.000 claims description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- QOMNJPSRBRDQSU-UHFFFAOYSA-N 5-aminobenzimidazol-2-one Chemical compound C1=C(N)C=CC2=NC(=O)N=C21 QOMNJPSRBRDQSU-UHFFFAOYSA-N 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 6
- 239000000243 solution Substances 0.000 claims 5
- 150000001340 alkali metals Chemical class 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 3
- 239000003963 antioxidant agent Substances 0.000 claims 3
- 230000003078 antioxidant effect Effects 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 239000000049 pigment Substances 0.000 claims 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 238000010494 dissociation reaction Methods 0.000 claims 2
- 230000005593 dissociations Effects 0.000 claims 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 2
- 229940079826 hydrogen sulfite Drugs 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 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 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 235000011941 Tilia x europaea Nutrition 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000008395 clarifying agent Substances 0.000 claims 1
- 239000012954 diazonium Substances 0.000 claims 1
- 150000001989 diazonium salts Chemical class 0.000 claims 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000004571 lime Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- 229950006098 orthocaine Drugs 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical class O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000004448 titration Methods 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- 235000019253 formic acid Nutrition 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
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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2518922A DE2518922C2 (de) | 1975-04-29 | 1975-04-29 | Verfahren zur Herstellung von 5- Acetoacetylaminobenzimidazolon-(2) |
| CH515476A CH603597A5 (enExample) | 1975-04-29 | 1976-04-23 | |
| NL7604355A NL7604355A (nl) | 1975-04-29 | 1976-04-23 | Werkwijze voor het bereiden van 5-acetoacetyl- aminobenzimidazolon. |
| IT22738/76A IT1062997B (it) | 1975-04-29 | 1976-04-27 | Processo per la preparazione di 5 acetacetilaminobenzimidazolone |
| IN735/CAL/1976A IN144220B (enExample) | 1975-04-29 | 1976-04-27 | |
| US05/680,719 US4087610A (en) | 1975-04-29 | 1976-04-27 | Process for the preparation of 5-acetoacetylamino-benzimidazolone |
| CA251,369A CA1058621A (en) | 1975-04-29 | 1976-04-28 | Process for the preparation of 5-acetoacetylamino benzimidazolone |
| JP51047929A JPS5910664B2 (ja) | 1975-04-29 | 1976-04-28 | ５−アセトアセチルアミノベンズイミダゾロンの製法 |
| FR7612714A FR2309542A1 (fr) | 1975-04-29 | 1976-04-29 | Procede de preparation d'acetoacetylamino-5 benzimidazolone |
| GB17484/76A GB1534077A (en) | 1975-04-29 | 1976-04-29 | Process for the preparation of 5-acetoacetylamino-benzimidazolone |
| BE166575A BE841284A (fr) | 1975-04-29 | 1976-04-29 | Procede de preparation d'acetoacetylamino-5 benzimidazolone |
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE2518922A1 DE2518922A1 (de) | 1976-11-18 |
| DE2518922C2 true DE2518922C2 (de) | 1982-08-19 |
Family
ID=5945233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2518922A Expired DE2518922C2 (de) | 1975-04-29 | 1975-04-29 | Verfahren zur Herstellung von 5- Acetoacetylaminobenzimidazolon-(2) |
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 |
| USRE25857E (en) * | 1961-09-14 | 1965-09-14 | Water-insoluble benzeneazo-s-aceto- acetylaminobenzimidazolone dye- stuffs | |
| 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 CH CH515476A patent/CH603597A5/xx not_active IP Right Cessation
- 1976-04-23 NL NL7604355A patent/NL7604355A/xx not_active Application Discontinuation
- 1976-04-27 IT IT22738/76A patent/IT1062997B/it active
- 1976-04-27 IN IN735/CAL/1976A patent/IN144220B/en unknown
- 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 BE BE166575A patent/BE841284A/xx not_active IP Right Cessation
- 1976-04-29 FR FR7612714A patent/FR2309542A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH603597A5 (enExample) | 1978-08-31 |
| FR2309542B1 (enExample) | 1980-08-01 |
| BE841284A (fr) | 1976-10-29 |
| IN144220B (enExample) | 1978-04-08 |
| JPS51131876A (en) | 1976-11-16 |
| GB1534077A (en) | 1978-11-29 |
| FR2309542A1 (fr) | 1976-11-26 |
| US4087610A (en) | 1978-05-02 |
| IT1062997B (it) | 1985-02-11 |
| NL7604355A (nl) | 1976-11-02 |
| DE2518922A1 (de) | 1976-11-18 |
| CA1058621A (en) | 1979-07-17 |
| JPS5910664B2 (ja) | 1984-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination |