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Chlordiazepozide (7-chloro-2-methylamino-5-phenyl-3-1,4-benzodiazepine 4-oxide) was the first benzodiazepine to enter the market as member of a new class of powerful tranquilizers. The of the hydrochloride was determined in 1979 (Herrnstadt , 1979), the structure of the pure compound in 1982 (Bertolasi , 1982). The reason for the study of chlordiazepoxide salts was the presence of three potential protonation sites (Herrnstadt 1979). In order to study a number of different chlordiazepoxide salts, we synthesized the compound according to the description by Sternbach (1961). The final step in this synthesis is the crystallization from dichloromethane. It turned out that the crystallization product that forms initially is a chlordiazepoxide dichloromethane solvate, whose structure is described here. The title compound (Fig. 1) features pairs of chlordiazepoxide molecules, which are hydrogen-bonded two symmetry-equivalent N–H···O bonds across an inversion centre (Fig. 2). The same pattern could be found in the hydrochloride (Herrnstadt , 1979). In the structure of pure chlordiazepoxide, pairs of molecules of the same (due to the high energy barrier of ring inversion, benzodiazepines are chiral) were observed and it was argued that this arrangement might be more stable than dimers of two different enantiomers. However, this effect must be quite subtle since the only interactions between the chlordiazepoxide and dichloromethane molecules are due to The dihedral angle between the two phenyl groups is 75.25 (6)°.

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Chlordiazepoxide was synthesized according to the procedure described by Sternbach (1961), starting from commercial 2-amino-5-chlorobenzophenone. Slow evaporation of the solution of the final product in dichloromethane yielded colourless, block-shaped crystals of the title compound. Once removed from the mother liquor, the crystals decomposed slowly (within days), yielding solvent-free chlordiazepoxide.

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For the synthesis of chlordiazepoxide, see: Sternbach (1961). For the structure of chlordiazepoxide, see: Bertolasi (1982). For the structure of a second polymorph of chlordiazepoxide, see: Singh (1998). For the structure of chlordiazepoxide hydrochloride, see: Herrnstadt (1979). For the early history of benzopdiazepines, see: Sternbach (1979).

For the synthesis of chlordiazepoxide, see: Sternbach (1961). For the structure of chlordiazepoxide, see: Bertolasi (1982). For the structure of a second polymorph of chlordiazepoxide, see: Singh (1998). For the structure of chlordiazepoxide hydrochloride, see: Herrnstadt (1979). For the early history of benzopdiazepines, see: Sternbach (1979).

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Chlordiazepozide (7-chloro-2-methylamino-5-phenyl-3-1,4-benzodiazepine 4-oxide) was the first benzodiazepine to enter the market as member of a new class of powerful tranquilizers. The of the hydrochloride was determined in 1979 (Herrnstadt , 1979), the structure of the pure compound in 1982 (Bertolasi , 1982). The reason for the study of chlordiazepoxide salts was the presence of three potential protonation sites (Herrnstadt 1979). In order to study a number of different chlordiazepoxide salts, we synthesized the compound according to the description by Sternbach (1961). The final step in this synthesis is the crystallization from dichloromethane. It turned out that the crystallization product that forms initially is a chlordiazepoxide dichloromethane solvate, whose structure is described here. The title compound (Fig. 1) features pairs of chlordiazepoxide molecules, which are hydrogen-bonded two symmetry-equivalent N–H···O bonds across an inversion centre (Fig. 2). The same pattern could be found in the hydrochloride (Herrnstadt , 1979). In the structure of pure chlordiazepoxide, pairs of molecules of the same (due to the high energy barrier of ring inversion, benzodiazepines are chiral) were observed and it was argued that this arrangement might be more stable than dimers of two different enantiomers. However, this effect must be quite subtle since the only interactions between the chlordiazepoxide and dichloromethane molecules are due to The dihedral angle between the two phenyl groups is 75.25 (6)°.

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A method for the synthesis of diazepam has been described (Sternbach et al., 1961). Benzoyl chloride reacts with p-chloroaniline to produce 2-amino-5-chlorobenzophenone. This is converted to the oxime with hydroxylamine. After cyclization with chloroacetyl chloride and ring enlargement with alkali treatment, 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one-4-oxide is reduced and methylated to diazepam.

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