7-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thione synthesis
- Product Name:7-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thione
- CAS Number:2894-71-5
- Molecular formula:C15H10Cl2N2S
- Molecular Weight:321.22
2894-67-9
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Yield:2894-71-5 81%
Reaction Conditions:
with Lawessons reagent in 1,2-dimethoxyethane at 80; for 5 h;
Steps:
4.1.4 Benzodiazepine-2-thiones 6a-d
A solution of 5a (114.8mg, 0.38mmol) in dimethoxyethane (1.9mL, 0.2M) containing Lawesson’s reagent (233.2mg, 0.58mmol) was stirred at 80°C for 5h. After the reaction was completed, the reaction mixture was cooled to rt and quenched with aq. NaHCO3. The reaction mixture was extracted with EtOAc (250mL), and the organic extract was washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography (hexane/EtOAc 2:1); yield: 98.6mg (81%); light yellow solid; mp 244-246°C (mp 252-253°C13, mp 240-241°C14b); Rf=0.40 (hexane/EtOAc 3:1). IR (ATR): 2959, 1474, 1179cm-1. 1H NMR (400MHz, CDCl3): δ 9.85 (br s, 1H), 7.54-7.52 (m, 1H), 7.46-7.36 (m, 4H), 7.11 (d, J=8.8Hz, 1H), 7.06 (d, J=2.4Hz, 1H), 4.81 (br s, 2H). 13C NMR (100MHz, CDCl3): δ 200.2, 168.9, 137.8, 137.2, 133.1, 131.9, 131.2, 131.2, 130.7, 130.5, 130.2, 129.6, 127.1, 122.2, 63.1. HRMS (ESI-TOF): m/z [M+H]+ calcd for C15H11N2SCl2: 321.0015; found: 321.0016.
References:
Tanaka, Ryoko;Makino, Kosho;Tabata, Hidetsugu;Oshitari, Tetsuta;Natsugari, Hideaki;Takahashi, Hideyo [Bioorganic and Medicinal Chemistry,2022,vol. 64,art. no. 116758]
2958-36-3
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14405-03-9
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