19359-28-5

Upstream product

• 101-92-8 4'-Chloroacetoacetanilide 
• 41295-64-1 4-chloroacetoacetyl chloride 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 135812-28-1 N-(4-Chlorophenyl)-5,6-dihydro-3-methyl-1,4-dithiin-2-carboxamide 
• 83570-69-8 5-Oxo-5H-3-thia-1,4,9b-triaza-cyclopenta[a]naphthalene-2-carboxylic acid (4-chloro-phenyl)-amide 
• 83570-65-4 C₁₅H₁₁Cl₂N₃O₃ 
• 83570-63-2 3-Thiocyanato-4'-chloracetoacetanilid 

Relevant academic research and scientific papers

Unexpected formation of new bicyclic γ-lactams by dimerization of α-chloroacetoacetanilides

Novel and unusual dimerization reaction of α-chloroacetoacetanilide under basic reaction condition to give structurally unique 6-oxa-3-azabicyclo[3.1.0]hexane was described.

Structure elucidation of N-aryl-2-chloro-3-oxobutanamides with respect to intra- and intermolecular hydrogen bonding

In general, N-aryl-2-chloro-3-oxobutanamides form in solid state an intermolecular hydrogen bond between the anilide hydrogen and the anilide carbonyl oxygen of a neighbouring molecule, which is disrupted in solution. An intramolecular association could not be detected.

Synthesis and structural assignment of oxanilo-N-arylhydrazonoyl chlorides

Oxanilo-N-arylhydrazonoyl chlorides have been prepared from appropriate N-aryl-2-chloro-3-oxobutanamides by the Japp-Klingemann reaction. The structures of the title compounds have been established in the solid state by single-crystal X-ray structure determination and IR spectroscopy, and in solution by IR, UV, and 1H and 13C NMR spectroscopy. The results indicate that the hydrazonoyl chloride moiety adopts the (Z)-configured form. In the crystal, intramolecular hydrogen bonds generally exist between the chloride function and the hydrazone hydrogen atom, and also between the amide hydrogen atom and the double-bonded nitrogen atom of the hydrazone moiety. In solution, this intramolecular hydrogen bonding could not be detected. In compounds with an ortho-chloro-substituted NH-aryl moiety, however, the chlorine atom is involved in hydrogen bonding to the NH hydrogen atom both in the crystal and in solution. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Process for the produciton of 2-chloroacetoacetic acid amides

Process for the production of 2-chloroacetoacetic acid amides. Diketene is converted at a temperature of +30° to -40° C. with the help of hydrogen chloride into acetoacetic acid chloride. Chlorine is introduced into the mixture at a temperature of +30° to -40° C., whereby 2-chloroacetoacetic acid chloride is formed. The latter is converted into the corresponding amide at a temperature of +50° to -40° C. by reaction with a N-compound having the formula: STR1 wherein (i) R=R'=H, or (ii) R=R'=alkyl, substituted alkyl, aryl, substituted aryl, alkyl aryl, substituted alkyl aryl, alkoxy aryl, substituted alkoxy aryl, alkoxy alkyl or substituted alkoxy alky, or (iii) R=H, and R'=alkyl, substituted alkyl, aryl, substituted aryl, alkyl aryl, substituted alkyl aryl, alkoxy aryl, substituted alkoxy aryl, alkoxy alkyl or substituted alkoxy alkyl.