ChemicalBook CAS DataBase List 7-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thione

7-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thione synthesis

5synthesis methods

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

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7-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thione

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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°C^14b); 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]

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