| | BENZP-DINITRIDE-THIO-KETONE Basic information |
| Product Name: | BENZP-DINITRIDE-THIO-KETONE | | Synonyms: | BENZP-DINITRIDE-THIO-KETONE;7-Chloro-5-phenyl-1H-benzo[e][1,4]diazepine-2(3H)-thione;Thionordiazepam;7-Chloro-5-phenyl-1H-benzo[e][1,4]diazepine-2(3H);7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione;Benzodiazepines Intermediate 1;2H-1,4-Benzodiazepine-2-thione, 7-chloro-1,3-dihydro-5-phenyl-;BENZP-DINIRIDE-THIO-KETONE | | CAS: | 4547-02-8 | | MF: | C15H11ClN2S | | MW: | 286.78 | | EINECS: | | | Product Categories: | Aromatics;Heterocycles;Sulfur & Selenium Compounds | | Mol File: | 4547-02-8.mol |  |
| | BENZP-DINITRIDE-THIO-KETONE Chemical Properties |
| Melting point | 256-258?C (dec.) | | Boiling point | 408.9±55.0 °C(Predicted) | | density | 1.32±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | DMF: 15 mg/ml; DMF:PBS (pH 7.2) (1:1): 0.5 mg/ml; DMSO: 10 mg/ml; Ethanol: 1 mg/ml | | form | A crystalline solid | | pka | 9.72±0.40(Predicted) |
| | BENZP-DINITRIDE-THIO-KETONE Usage And Synthesis |
| Chemical Properties | Yellow Solid | | Uses | 7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione (cas# 4547-02-8) is a positive allosteric modulator for the muscarinic M1 receptor, which could be a potential treament for the Alzheimer's disease or Schizophrenia. | | Synthesis | Under nitrogen protection, 975 g of toluene, 160 g of triethylamine and 204 g (0.92 mol) of phosphorus pentasulfide were added to a dry reaction flask and stirred until the solution was clarified, then 230 g (0.85 mol) of nortrazepam was added. The reaction mixture was heated to 75°C and maintained for 8 hours. After completion of the reaction, it was cooled to room temperature, filtered and dried to obtain light yellow crystals 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione (M5) 195g in 80% yield and >94% HPLC purity.
The purification step of the crude product M5 obtained from the above preparation: at room temperature, the crude product was dissolved with an equal weight of N,N-dimethylformamide and filtered to remove insoluble matter. Subsequently, water of equal mass with N,N-dimethylformamide was added for recrystallization, and after M5 was completely recrystallized, it was filtered and dried to obtain 175 g of light yellow or nearly yellow crystalline powder, with a purification rate of 90% and an HPLC content of ≥98.5%. | | References | [1] Synthesis, 1987, # 2, p. 162 - 164
[2] Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 1, p. 123-136)
[3] Synthesis, 2004, # 16, p. 2697 - 2703
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 20, p. 5984 - 5987
[5] Patent: CN104130201, 2016, B. Location in patent: Paragraph 0019; 0025; 0026; 0027; 0028 |
| | BENZP-DINITRIDE-THIO-KETONE Preparation Products And Raw materials |
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