101363-10-4
RUFLOXACIN
CAS: 101363-10-4
Molecular Formula: C17H18FN3O3S
101363-10-4 - Names and Identifiers
101363-10-4 - Physico-chemical Properties
| Molecular Formula | C17H18FN3O3S |
| Molar Mass | 363.41 |
| Density | 1.54 |
| Boling Point | 574.6±50.0 °C(Predicted) |
| pKa | 5.21±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Physical and Chemical Properties | Chemical Properties Rufloxacin Hydrochloride (Rufloxacin Hydrochloride):C17H18FN3O3S?HCl. [106017-08-7]. Crystallized in ethanol-water with melting point 322~324 ℃. Acute toxicity LD50 rabbits, male rats, female rats (mg/kg):660,631,501 oral. |
| Use | Use for long-acting quinolone antibacterial drugs. The grass blue positive and negative bacteria, especially for Enterobacter has significant antibacterial activity. Pseudomonas aeruginosa, Group D Streptococcus and most anaerobic bacteria resistant to this product. The bacterial prostatitis has high curative effect, good tolerance. For sensitive bacteria caused by urinary tract infection, lower respiratory tract infection. |
101363-10-4 - Production method
Method 1: 2, 4-difluoro-3-chloronitrobenzene is obtained by fluorination from 2,3, 4-trichloronitrobenzene, which is condensed with mercaptoethanol and then reduced, brominated, and cyclized to obtain benzothiazide. Benzothiazine is condensed with EMME, and then Gould.Jacobs cyclization reaction to form a quinolone parent ring, and then hydrolysis, oxidation, condensation and reduction with N-methylpiperazine to obtain rufloxacin. Rufloxacin hydrochloride can be obtained by forming salt with hydrochloric acid.
2, 4-difluoro-3-chloronitrobenzene can also be condensed with ethyl mercaptoacetate, and then reduced and cyclized by nitro to obtain benzothiazines.
Method 2: Ethyl tetrafluorobenzoyl acetate was prepared from 2,3,4,5-tetrafluorobenzoic acid as the starting material, then condensed with N-methylpiperazine, then reacted with N,N-dimethylformamide dimethanol (DMFA), then replaced, intramolecular nucleophilic substitution, cyclized to form quinolone parent ring, and then hydrolyzed into salt to obtain rufloxacin hydrochloride.
Methods 3:2,3, 4-trifluoronitrobenzene and 2-mercaptoethanol were dissolved in absolute ethanol, triethylamine was added dropwise below 0 ℃, and the reaction was complete. Concentrate under reduced pressure, add water, and extract with chloroform. The extract is concentrated to obtain intermediate (I), which is directly used in the next reaction.
Intermediate (I), ethanol, ammonium chloride and water are mixed, iron powder and dilute hydrochloric acid are added at 40°C, and the reaction is complete. The ethanol is recovered, extracted with ethyl acetate, and concentrated to obtain intermediate (II).
Intermediate (II) and 40% hydrobromic acid react to complete at 120°C. Hydrobromic acid was distilled under reduced pressure to obtain intermediate (Ⅲ).
The intermediate (Ⅲ) is mixed with ethanol, heated, adjusted to Ph = 9 with sodium carbonate, and reacted at 50 ℃. Recover ethanol, extract with chloroform, and concentrate to obtain intermediate (Ⅳ).
The intermediate (Ⅳ) and EMMF were reacted at 120 ℃, PPA was added, and the reaction was raised to 160 ℃. Cool, add water, and warm again. Cooling, filtering solid, recrystallizing with dimethylformamide to obtain intermediate (V) with 69% yield. The intermediate (V) was mixed with 40% fluoroboric acid and reacted at about 50°C. Cooling, filtration, recrystallization with dimethylformamide and methanol (5:2) to obtain intermediate (VI) with 96% yield.
The intermediate (VI), N-methylpiperazine, triethylamine and dimethylformamide were reacted at 50~60 ℃. Recover the solvent, add 5% sodium hydroxide solution to dissolve the residue, and filter. The filtrate was adjusted to Ph = 7 with 2mol/L hydrochloric acid. Filter the solid and recrystallize with 30% ethanol to obtain rufloxacin with 76.9% yield and melting point 300~301 ℃
Last Update：2024-04-09 21:01:54
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CAS: 101363-10-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
CAS: 101363-10-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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