205309-72-4

Upstream product

• 25784-91-2 2-chloro-5-nitrobenzoylchloride 
• 25808-30-4 2-(methylamino)acetonitrile hydrochloride 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 

Relevant academic research and scientific papers

Substituted N-Cyanomethyl-2-halo-N-methylarenecarboxamides as Precursors of 1,4-Benzothiazepines

2-Halogeno substituted N-cyanomethyl-N-methylbenzamides 1a-1i were investigated in a correlation analysis by ir spectroscopy to determine the conformational behavior. Compound 1h gives 4-methyl-2-methylthio-8-nitro-5-oxo-4,5-dihydro-1,4-benzothiazepine-3- carbonitrile 3 by dithiocarboxylation procedure whereas 1b was not able to react to heterocyclic seven-membered ring system.

A facile synthesis of substituted 1,4-benzothiazepin-5(4H)-ones and pyrido[3,2-f][1,4]thiazepin-5(4H)-ones - crystal and molecular structure of 2-ethylthio-4-methyl-5(4H)-oxopyrido[3,2-f][1,4]thiazepine-3-carbonitrile

A new synthesis of pyrido[3,2-f][1,4]thiazepine derivatives 3 starting with 2-chloronicotinic acid (1), methylaminoacetonitrile hydrochloride and carbon disulfide is described. As proved by a crystal structure determination, a boat conformation with approximated mirror symmetry can be assigned to the 1,4-thiazepine ring in 3b. 2-Chloro-N-cyanomethyl-N-methyl-5-nitrobenzamide (5) reacts with carbon disulfide in presence of a strong base in DMF or DMSO depending on the temperature to either the benzothiopyran compound 6 or by intramolecular aromatic nucleophilic substitution to a seven-membered ring system as thiolate anion which can be alkylated to give the 1,4-benzothiazepine derivative 7, or to an open-chain amido ketene dithioacetal 8.