CA1132582A - Process for the preparation of 5-nitrobenzimidazolone-(2) - Google Patents
Process for the preparation of 5-nitrobenzimidazolone-(2)Info
- Publication number
- CA1132582A CA1132582A CA345,289A CA345289A CA1132582A CA 1132582 A CA1132582 A CA 1132582A CA 345289 A CA345289 A CA 345289A CA 1132582 A CA1132582 A CA 1132582A
- Authority
- CA
- Canada
- Prior art keywords
- nitric acid
- benzimidazolone
- weight
- concentration
- nitrobenzimidazolone
- 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 abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 29
- 238000006396 nitration reaction Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012452 mother liquor Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000987 azo dye Substances 0.000 abstract description 3
- 230000008878 coupling Effects 0.000 abstract description 2
- 238000010168 coupling process Methods 0.000 abstract description 2
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 2
- 239000000049 pigment Substances 0.000 abstract description 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 abstract 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 239000002351 wastewater Substances 0.000 abstract 1
- 229940074355 nitric acid Drugs 0.000 description 20
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 9
- 238000013019 agitation Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 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 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- -1 amino compound Chemical class 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- KMIFZILWRRENBO-UHFFFAOYSA-N 4-nitrobenzimidazol-2-one Chemical compound [O-][N+](=O)C1=CC=CC2=NC(=O)N=C12 KMIFZILWRRENBO-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008641 benzimidazolones Chemical class 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940045136 urea Drugs 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792905126 DE2905126A1 (de) | 1979-02-10 | 1979-02-10 | Verfahren zur herstellung von 5-nitrobenzimidazolon-(2) |
| DEP2905126.1 | 1979-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1132582A true CA1132582A (en) | 1982-09-28 |
Family
ID=6062649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA345,289A Expired CA1132582A (en) | 1979-02-10 | 1980-02-08 | Process for the preparation of 5-nitrobenzimidazolone-(2) |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0014449B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS55111471A (enrdf_load_stackoverflow) |
| AU (1) | AU530061B2 (enrdf_load_stackoverflow) |
| BR (1) | BR8000800A (enrdf_load_stackoverflow) |
| CA (1) | CA1132582A (enrdf_load_stackoverflow) |
| DE (2) | DE2905126A1 (enrdf_load_stackoverflow) |
| IN (1) | IN150238B (enrdf_load_stackoverflow) |
| MX (1) | MX152429A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329273A (zh) * | 2017-12-21 | 2018-07-27 | 山东汇海医药化工有限公司 | 一种二次硝化合成5-硝基苯并咪唑酮的方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4334269B2 (ja) * | 2002-04-18 | 2009-09-30 | 株式会社ワイケイワイ | ゴルフ用クラブの展示用支持装置 |
-
1979
- 1979-02-10 DE DE19792905126 patent/DE2905126A1/de not_active Withdrawn
-
1980
- 1980-02-04 DE DE8080100536T patent/DE3062853D1/de not_active Expired
- 1980-02-04 EP EP80100536A patent/EP0014449B1/de not_active Expired
- 1980-02-04 IN IN130/CAL/82A patent/IN150238B/en unknown
- 1980-02-08 CA CA345,289A patent/CA1132582A/en not_active Expired
- 1980-02-08 AU AU55346/80A patent/AU530061B2/en not_active Expired
- 1980-02-08 JP JP1379280A patent/JPS55111471A/ja active Granted
- 1980-02-08 MX MX181118A patent/MX152429A/es unknown
- 1980-02-08 BR BR8000800A patent/BR8000800A/pt not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329273A (zh) * | 2017-12-21 | 2018-07-27 | 山东汇海医药化工有限公司 | 一种二次硝化合成5-硝基苯并咪唑酮的方法 |
| CN108329273B (zh) * | 2017-12-21 | 2021-05-18 | 山东汇海医药化工有限公司 | 一种二次硝化合成5-硝基苯并咪唑酮的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0014449A3 (en) | 1980-09-03 |
| MX152429A (es) | 1985-07-15 |
| DE3062853D1 (de) | 1983-06-01 |
| EP0014449B1 (de) | 1983-04-27 |
| JPS6326752B2 (enrdf_load_stackoverflow) | 1988-05-31 |
| AU5534680A (en) | 1980-08-14 |
| IN150238B (enrdf_load_stackoverflow) | 1982-08-21 |
| DE2905126A1 (de) | 1980-08-21 |
| BR8000800A (pt) | 1980-10-29 |
| EP0014449A2 (de) | 1980-08-20 |
| JPS55111471A (en) | 1980-08-28 |
| AU530061B2 (en) | 1983-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |