DE2612391C2 - Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-(2) - Google Patents
Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-(2)Info
- Publication number
- DE2612391C2 DE2612391C2 DE2612391A DE2612391A DE2612391C2 DE 2612391 C2 DE2612391 C2 DE 2612391C2 DE 2612391 A DE2612391 A DE 2612391A DE 2612391 A DE2612391 A DE 2612391A DE 2612391 C2 DE2612391 C2 DE 2612391C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- diketene
- water
- product
- amino
- 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 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 25
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000000047 product Substances 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QOMNJPSRBRDQSU-UHFFFAOYSA-N 5-aminobenzimidazol-2-one Chemical compound C1=C(N)C=CC2=NC(=O)N=C21 QOMNJPSRBRDQSU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- -1 Benzene-substituted acetoacetylamino-benzimidazolones Chemical class 0.000 description 2
- 241000792859 Enema Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 239000007920 enema Substances 0.000 description 2
- 229940095399 enema Drugs 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CRXVBLLLPNWFBS-UHFFFAOYSA-N 4-aminobenzimidazol-2-one Chemical class NC1=CC=CC2=NC(=O)N=C12 CRXVBLLLPNWFBS-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000000809 air pollutant Substances 0.000 description 1
- 231100001243 air pollutant Toxicity 0.000 description 1
- 238000004887 air purification Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002860 competitive effect Effects 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
- 230000007812 deficiency Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002913 oxalic acids Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000011144 upstream manufacturing Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2612391A DE2612391C2 (de) | 1976-03-24 | 1976-03-24 | Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-(2) |
| CH352677A CH629193A5 (de) | 1976-03-24 | 1977-03-21 | Verfahren zur herstellung von 5-acetoacetylaminobenzimidazolon. |
| US05/780,221 US4153798A (en) | 1976-03-24 | 1977-03-22 | Process for the manufacture of 5-acetoacetylamino-benzimidazolone |
| JP52031216A JPS6014031B2 (ja) | 1976-03-24 | 1977-03-23 | ５−アセトアセチルアミノ−ベンゾイミダゾロンの製法 |
| GB7712435A GB1541970A (en) | 1976-03-24 | 1977-03-24 | Process for the manufacture of 5-acetoacetylamino-benzimidazolone |
| FR7708782A FR2345434A1 (fr) | 1976-03-24 | 1977-03-24 | Procede de preparation de la 5-acetoacetylamino-benzimidazolone |
| BE176094A BE852850A (fr) | 1976-03-24 | 1977-03-24 | Procede de preparation de la 5-acetoacetyl-amino-benzimidazolone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2612391A DE2612391C2 (de) | 1976-03-24 | 1976-03-24 | Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-(2) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2612391A1 DE2612391A1 (de) | 1977-10-06 |
| DE2612391C2 true DE2612391C2 (de) | 1982-09-23 |
Family
ID=5973269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2612391A Expired DE2612391C2 (de) | 1976-03-24 | 1976-03-24 | Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-(2) |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4153798A (enExample) |
| JP (1) | JPS6014031B2 (enExample) |
| BE (1) | BE852850A (enExample) |
| CH (1) | CH629193A5 (enExample) |
| DE (1) | DE2612391C2 (enExample) |
| FR (1) | FR2345434A1 (enExample) |
| GB (1) | GB1541970A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19747175A1 (de) * | 1997-10-24 | 1999-04-29 | Clariant Int Ltd | Chlorhaltige Triphendioxazin-Verbindungen |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4335614A1 (de) * | 1993-10-19 | 1995-04-27 | Hoechst Ag | Verfahren zur Herstellung von 5-Acetoacetylaminobenzimidazolon-2 |
| US6617453B1 (en) | 1997-10-24 | 2003-09-09 | Clariant Finance (Bvi) Limited | Triphendioxazine compounds |
| DE19913401A1 (de) | 1999-03-25 | 2000-09-28 | Clariant Gmbh | Verfahren zur Herstellung von Dioxazin-Verbindungen |
| DE10303581A1 (de) * | 2003-01-30 | 2004-08-12 | Clariant Gmbh | Acetoacetylierung von Alkoholen, Thiolen und Aminen im Mikroreaktor |
| 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 |
| CN110183385A (zh) * | 2019-07-01 | 2019-08-30 | 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纯度的方法 |
| 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 |
Family Cites Families (10)
| 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 |
| US3304328A (en) * | 1963-10-25 | 1967-02-14 | Fmc Corp | Preparation of acetoacetarylamides |
| DE1644231A1 (de) * | 1967-10-27 | 1970-12-10 | Hoechst Ag | Wasserunloeslicher Monoazofarbstoff und Verfahren zu seiner Herstellung |
| US3555003A (en) * | 1968-10-22 | 1971-01-12 | Hoechst Ag | Water-insoluble benzimidazolone containing monoazo dyestuffs |
| US3963694A (en) * | 1971-03-03 | 1976-06-15 | Ciba-Geigy Corporation | Hydroxyquinolyl- and quinazolonylazoacetoacetylbenzimidazolone pigments |
| DE2518922C2 (de) * | 1975-04-29 | 1982-08-19 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 5- Acetoacetylaminobenzimidazolon-(2) |
-
1976
- 1976-03-24 DE DE2612391A patent/DE2612391C2/de not_active Expired
-
1977
- 1977-03-21 CH CH352677A patent/CH629193A5/de not_active IP Right Cessation
- 1977-03-22 US US05/780,221 patent/US4153798A/en not_active Expired - Lifetime
- 1977-03-23 JP JP52031216A patent/JPS6014031B2/ja not_active Expired
- 1977-03-24 GB GB7712435A patent/GB1541970A/en not_active Expired
- 1977-03-24 BE BE176094A patent/BE852850A/xx not_active IP Right Cessation
- 1977-03-24 FR FR7708782A patent/FR2345434A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19747175A1 (de) * | 1997-10-24 | 1999-04-29 | Clariant Int Ltd | Chlorhaltige Triphendioxazin-Verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2612391A1 (de) | 1977-10-06 |
| FR2345434A1 (fr) | 1977-10-21 |
| GB1541970A (en) | 1979-03-14 |
| CH629193A5 (de) | 1982-04-15 |
| JPS6014031B2 (ja) | 1985-04-11 |
| US4153798A (en) | 1979-05-08 |
| BE852850A (fr) | 1977-09-26 |
| JPS52116467A (en) | 1977-09-29 |
| FR2345434B1 (enExample) | 1984-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination |