2153-09-5

Upstream product

• 146935-65-1 2,2-dichloro-N-isopropenyl-N-(4-methoxyphenyl)acetamide 
• 79-36-7 dichloroacethyl chloride 
• 104-94-9 4-methoxy-aniline 
• 5437-98-9 4'-methoxyacetoacetanilide 
• 103239-04-9 N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine 
• 40938-34-9 isopropylidene-(4-methoxyphenyl)amine 

Relevant academic research and scientific papers

Unexpected Formation of 2,2-Dichloro-N-(chloromethyl)acetamides during Attempted Staudinger 2,2-Dichloro-β-lactam Synthesis

In the quest for 3,3-dichloro-β-lactam building blocks, the serendipitous formation of 2,2-dichloro-N-(chloromethyl)acetamides was observed. This peculiar reactivity was investigated in detail, both experimentally and computationally by means of Density Functional Theory (DFT) calculations. 2,2-Dichloro-N-(chloromethyl)acetamides were thus shown to be formed experimentally through reaction of 2,2-dichloroacetyl chloride with glyceraldehyde-derived imines, i. e. (2,2-dimethyl-1,3-dioxolan-4-yl)methanimines, bearing aromatic N-substituents, in the presence as well as in the absence of a base. Deployment of aliphatic imines, however, resulted in complex reaction mixtures, pointing to the importance of a stabilizing aromatic substituent at nitrogen. The DFT results indicate that the substituents can alter the governing equilibria on the one hand and intrinsic barrier heights for the different routes on the other hand, showing that these are controlling the reaction outcome. Furthermore, the 2,2-dichloro-N-(chloromethyl)acetamides proved to be rather unstable in solution and thus difficult to isolate. Nonetheless, their molecular structure was confirmed by means of NMR analysis of several purified analogs and X-ray study of a 4-methoxyphenyl derivative.

Dichloromeldrum's acid (DiCMA): A practical and green amine dichloroacetylation reagent

Dichloromeldrum's acid is introduced as a bench-stable, nonvolatile reagent for the dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

Zwitterion-Catalyzed Deacylative Dihalogenation of β-Oxo Amides

α,α-Dihalo-N-arylacetamides are commonly used as intermediates in various organic reactions. In the study described here, a catalytic synthesis of α,α-dihalo-N-arylacetamides from β-oxo amides was developed using zwitterionic catalysts and N-halosuccinimi

Divergent synthesis of α,α-dihaloamides through α,α-dihalogenation of β-oxo amides by using N-halosuccinimides

An efficient and divergent one-pot synthesis of α,α- dihaloamides from readily available β-oxo amides based on the selection of reaction conditions is reported. α,α-Dihalo-β-oxo amides were produced by treating β-oxo amides with N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS) in water at room temperature, whereas α,α-dihaloacetamides were synthesized by subjecting β-oxo amides to NCS or NBS in ethanol under reflux. A divergent synthesis of α,α-dihalo-β-oxo amides and α,α-dihaloacetamides has been developed from readily available β-oxo amides. Upon treatment with N-halosuccinimides in water at room temperature, α,α-dihalo-β- oxo amides were produced, whereas dihaloacetamides were synthesized by treatment of β-oxo amides with N-halosuccinimides in ethanol under reflux. Copyright

Approach for the direct synthesis of β-dichlorosubstituted acetanilides using iodine trichloride (ICl3) as the oxidant and catalyst

A reliable method for direct synthesis of β-dichlorosubstituted acetanilides is reported. The key transformation involves the oxidative and catalytic cleavage of a carbon-carbon bond in the presence of iodine trichloride (ICl3). In this protoco

Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxobutanamides to 2,2-dihalo-N-phenylacetamides

A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon-carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method s

Novel N-phenyl dichloroacetamide derivatives as anticancer reagents: Design, synthesis and biological evaluation

A current study shows that sodium dichloroacetate (DCA) can induce cancer cell apoptosis and inhibit tumor growth, but its cytotoxic activity is low (IC50 > 1000 μM for A549). In this paper, a variety of DCA derivatives were synthesized, and their cytotoxic activities were evaluated. The result showed that the N-phenyl-2,2-dichloroacetamide analogues had satisfactory potencies. Among them, N-(3-iodophenyl)-2,2-dichloroacetamide (3e), an optimized lead compound, has an IC50 against A549 as low as 4.76 μM. Furthermore, it can induce cancer cell apoptosis and has a low toxicity in mice (LD50 = 1117 mg/kg). N-phenyl-2,2-dichloroacetamide analogues has higher cytotoxic activity and N-(3-iodophenyl)-2,2-dichloroacetamide (3e) is an optimized lead compound.

REACTIONS OF DICHLOROCARBENE WITH ARYLIMINES OF ALIPHATIC KETONES

In the reactions of arylimines of ketones with dichlorocarbene substituted N-aryl-N-vinylformamides are formed, and to these the carbene then adds at the C=C bond.The proces includes a stage in which hydrogen is transferred in the intermediate imonium-dichloromethylidene fragment from the β-carbon atom to the dichloromethylene fragment.