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Reclazepam
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-[7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1,4-benzodiazepin-1-yl]-1,3-oxazol-4-one;
CAS Number	76053-16-2 ;
PubChem CID	3052777;
ChemSpider	2314554 ;
UNII	YJL42911RA;
KEGG	D05710 ;
CompTox Dashboard (EPA)	DTXSID50226955 ;
Chemical and physical data
Formula	C18H13Cl2N3O2
Molar mass	374.22 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccccc1/C4=N/CCN(C\2=N\C(=O)CO/2)c3ccc(Cl)cc34;
	InChI InChI=1S/C18H13Cl2N3O2/c19-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)20)21-7-8-23(15)18-22-16(24)10-25-18/h1-6,9H,7-8,10H2 ; Key:MQGIGGJUPITZSE-UHFFFAOYSA-N ;
	(verify)

Reclazepam is a drug which is a benzodiazepine derivative. It has sedative and anxiolytic effects similar to those produced by other benzodiazepine derivatives, and has a short duration of action.^[1]

Synthesis

The reduction of the lactam in Delorazepam with lithium aluminium hydride gives CID:20333776 (1). Condensation with 2-chloroacetylisocyanate [4461-30-7] (2) proceeds to afford urea, CID:20333773 (3). Reaction of that with sodium iodide and base probably proceeds initially by halogen exchange of iodine for chlorine (Finkelstein reaction). Subsequent replacement of iodide by the enol anion of the urea oxygen results in formation of the oxazolone ring. There is thus obtained reclazepam (4).

References

^ "Reclazepam". Pscyhotropics.dk. 20 January 1986. Retrieved 24 August 2009.^{[dead link]}
^ US 4208327, Yonan PK, "5-Aryl-1-(2-oxazolin-2-yl)-1H-1,4-benzodiazepines and related compounds", issued 17 June 1980, assigned to GD Searle LLC.
^ Speziale AJ, Smith LR (April 2003). "α‐Chloroacetyl Isocyanate: Isocyanic acid, anhydride with chloroacetic acid". Organic Syntheses. 46: 16. doi:10.1002/0471264180.os046.05.
^ US 3144439, Reeder E, Sternbach LH, "Process for production of benzodiazepines", issued 1964, assigned to Hoffmann-La Roche Inc