The preparation of a number of 1,4-benzodiazepines substituted in the 3 position is described. The rearrangement of 7-chloro-l,3-dihydro-5-phenyl-2H-l,4-benzodiazepin-2-one 4-oxide with diacetyl sulfide yields largely the 3-acetylthio compound. Amines, ethers, and sulfides were prepared through the chloro intermediate. A 3-carbethoxybenzodiazepine was prepared and converted into oxazepam. The pharmacological test data of new and previously published compounds are given.
A mixture melting point with authentic material prepared as described19 showed m.p. 103-105°. The infrared spectra of the two compounds were superimposable.Decarboxylation of II to Give I.-A mixture of 1 g. of II and 1 g. of copper powder in 25 ml. of quinoline was heated under reflux for 3 hr. The mixture was filtered, 50 ml. of chloroform was added, and the organic phase was washed in turn with N hydrochloric acid and water. The organic phase was dried and
A number of thiazolo 5‐carboxylic acid derivatives were prepared which were fused to other heterocycles such as 1,2,4‐benzothiadiazine, quinazoline, and pyrimidine rings at the 2,3‐position of the thiazole ring. In several instances unexpected products were obtained, depending on the reaction conditions. The chemistry of these reactions and the identification of the products are discussed.
Some Analogs of Chlordiazepoxide 63 mixture was then heated under reflux for 2.5 hr., kept 16 hr.; the solid filtered, the filtrate cooled, and extracted with 750 ml. of cold 20% hydrochloric acid. With continued ice-cooling, the acid extract was made alkaline with solid potassium carbonate and the base extracted with ether. Concentration of the dried ether extract and distillation of the residue gave 142.3 g. (81% yield) of the base, b.p. 57-60°( 1 mm.), h«d 1.4773.
Aus dem 2‐Amino‐benzolsulfonamid (I) und Thiophosgen (II) entsteht das Benzothiadiazin = dioxid (III), das mit α‐Chlor‐acetoacetat (IV) zu (V) kondensiert wird.
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