| Identification | Back Directory | [Name]
BENZP-DINITRIDE-THIO-KETONE | [CAS]
4547-02-8 | [Synonyms]
Thionordiazepam
Alprazolam Impurity 17
BENZP-DINIRIDE-THIO-KETONE
BENZP-DINITRIDE-THIO-KETONE
Benzodiazepines Intermediate 1
7-Chloro-5-phenyl-1H-benzo[e][1,4]diazepine-2(3H)
7-Chloro-5-phenyl-1H-benzo[e][1,4]diazepine-2(3H)-thione
7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione
2H-1,4-Benzodiazepine-2-thione, 7-chloro-1,3-dihydro-5-phenyl- | [Molecular Formula]
C15H11ClN2S | [MDL Number]
MFCD02068928 | [MOL File]
4547-02-8.mol | [Molecular Weight]
286.78 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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 |
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