Alternatived Products of [ 13182-87-1 ]
Product Details of [ 13182-87-1 ]
| CAS No. : | 13182-87-1 |
MDL No. : | MFCD00425441 |
| Formula : |
C10H13N3O6
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
271.23
|
Pubchem ID : | - |
| Synonyms : |
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Safety of [ 13182-87-1 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 13182-87-1 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Upstream synthesis route of [ 13182-87-1 ]
- Downstream synthetic route of [ 13182-87-1 ]
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[ 108-30-5 ]
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[ 443-48-1 ]
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[ 13182-87-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 95% |
With dmap In acetonitrile for 48h; Ambient temperature; |
|
| 95% |
With pyridine at 20℃; for 24h; Inert atmosphere; Cooling with ice; |
|
| 94% |
With sodium hydroxide In methanol; water at 60℃; for 2h; |
1
In a 100mL reactor with lOmL of methanol at a temperature about 60°C, add 0.315g of metronidazole, 2. OmL of NaOH 1N, 0.2g of succinic anhydride and keep the reaction medium under stirring and heating for about 2 hours. Cool the reaction medium to a temperature around 8°C and allow it to stand for 12 hours. The reaction medium is filtered and the solvent is evaporated to dryness yielding 0.47g of metronidazole monosuccinate. (Yield = 94%) |
| 90% |
With dmap In acetonitrile at 20℃; for 72h; |
4.2.1. General procedure for preparation of metronidazole hemiesters (2-3)
General procedure: Hemiesters 2 (MTZ-SUC) and 3 (MTZ-GLU) were obtained according to literature procedures with slight modifications refPreviewPlaceHolder[33]. Briefly, MTZ (11.7 mmol) and succinic or glutaric anhydride (13.7 mmol) were dissolved in 80 ml of acetonitrile. The obtained solutions were stirred at room temperature respectively for 72 or 120 h in presence of 4-dimethylaminopyridine (DMAP) as catalyst. The reaction was monitored by TLC. The solvent was evaporated in a rotary evaporator to give a residue that was washed three times with 25 ml of hot water (60 °C) and let to crystallize as a white solid powder. The precipitate was filtered off and dried in a P2O5 desiccator under vacuum to give the hemiesters (2-3). |
| 87% |
With pyridine for 0.1h; Microwave irradiation; |
|
| 75% |
With dmap In acetonitrile Ambient temperature; |
|
|
With dmap In acetonitrile |
|
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With pyridine at 100℃; for 16h; |
Synthesis of Metronidazole Hemisuccinate (MNZ-SA):
Add 0.85 g of metronidazole, 1.25 g of succinic anhydride, and 5 mL of anhydrous pyridine into a 10 mL reaction flask. After stirring on a magnetic stirrer, heat and stir at 100°C For 16 hours, the pyridine was evaporated under reduced pressure, 5 mL ice water was added, and the mixture was extracted with chloroform pre-cooled at 4°C. The chloroform was evaporated under reduced pressure and evaporated to dryness at room temperature.Cooled chloroform, washed twice with ice water, dehydrated with anhydrous sodium sulfate, evaporated under reduced pressure to remove chloroform, evaporated to dryness at room temperature to obtain needle-like white crystals, namely metronidazole hemisuccinate (MNZ-SA) |
Reference：
[1]Vermeersch; Vandoorne; Permentier; Schacht
[Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 8, p. 591 - 596]
[2]Wubulikasimu, Muyasier; Muhammad, Turghun; Imerhasan, Mukhtar; Hudaberdi, Nurmemet; Yang, Wenwu; Zhao, Jianzhang; Peng, Xiaojun
[RSC Advances, 2019, vol. 9, # 12, p. 6779 - 6784]
[3]Current Patent Assignee: EMS BR SP - WO2005/41853, 2005, A2
Location in patent: Page/Page column 26
[4]Location in patent: experimental part
Mura, Carla; Valenti, Donatella; Floris, Costantino; Sanna, Roberta; De Luca, Maria Antonietta; Fadda, Anna Maria; Loy, Giuseppe
[European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4142 - 4150]
[5]Location in patent: experimental part
Luo, Xin-Feng; He, Ling; Yin, Hai-Bin; Zheng, Hu; Bei, Di; Deng, Jin-Jin; Huang, Wen-Cai
[Synthetic Communications, 2009, vol. 39, # 19, p. 3444 - 3452]
[6]Mahfouz, Nadia M.; Aboul-Fadl, Tarek; Diab, Ahmed K.
[European Journal of Medicinal Chemistry, 1998, vol. 33, # 9, p. 675 - 683]
[7]Aboul-Fadl, Tarek; Mahfouz, Nadia M.
[Scientia Pharmaceutica, 1998, vol. 66, # 4, p. 309 - 324]
[8]Current Patent Assignee: W.H.P.M. BIORESEARCH AND TECHNOLOGY CO LTD - CN111228481, 2020, A
Location in patent: Paragraph 0035-0037
- 2
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[ 83-73-8 ]
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[ 13182-87-1 ]
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[ 220819-23-8 ]
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[ 220819-23-8 ]
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[ 83-73-8 ]
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[ 110-15-6 ]
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[ 443-48-1 ]
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[ 13182-87-1 ]
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