N-Benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide

Abstract

The title compound, N-benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide (1) was synthesized by reacting 3-trifluoromethylbenzoyl chloride (4) and 4-aminobenzo[c][1,2,5]thiadiazole (5). The compound was characterized by various spectroscopic methods (1H NMR, 13C NMR, IR, GC-MS) and its composition confirmed by elemental analysis. The importance of this compound lies in its possession of an N,N-bidentate directing group. Such a structural motif is potentially suitable for metal-catalyzed C-H bond functionalization reactions.

N-(2-Hydroxy-1,1-dimethylethyl)-3-methylbenzamide

“…We wish to report herein a standard synthesis of the title compound, N-(2-hydroxy-1,1dimethylethyl)-3-methylbenzamide (11), from the corresponding benzoyl chloride or benzoic acid. The compound was full characterized by various spectroscopic methods, elemental analysis, and its structure was determined and confirmed by X-ray analysis (Please see the supporting information for spectra and other supporting materials).…”

“…Thus, 3-methylbenzolyl chloride (10, Scheme 3) was reacted with 2-amino-2-methyl-1propanol (7, Scheme 3) under standard amide formation reaction conditions to give the corresponding amide in isolated 62% yield. For comparison purposes, the target compound (11) was also obtained using a carboxylic acidamine coupling method. Thus the 3-methylbenzoic acid (12, Scheme 4) was treated with the coupling agent; DCC (dicyclohexylcarbodiimide) and 2-amino-2-methyl-1-propanol (7) in the presence of DMAP (4-N,N-dimethylaminopyridine) to give the desired title compound, N- (2- The product was characterized by various spectroscopic methods; 1 H NMR, 13 C NMR, IR, GC-MS, and its elemental composition was confirmed by elemental analysis.…”

“…Thus, amides containing hydroxymethyl(dimethylmethyl) were envisaged (6, Scheme 1) which would have as a retrosynthetic precursor 2-amino-2-methyl-1propanol 7 (Scheme 1). Based on the strategic design considerations above and as part of our research program on the development of design-based bidentate directing groups, [11] we initiated synthesis of amides containing 2-amino-2-methyl-1-propanol as a potential N,O-bidentate directing group. The aim would ultimately be to test such amides in metal-catalyzed C-H bond functionalization reactions.…”

“…Hydroxy-1,1-dimethylethyl)-3-methylbenzamide(11) 3-Methylbenzoyl chloride (10) (1.30 mL, 9.86 mmol) was added dropwise under an atmosphere of N 2 into a cold (0 • C ice-water bath) solution of 2-amino-2-methylpropan-1-ol (7) (0.50 mL, 5.2 mmol), in CH 2 Cl 2 (20 mL). Triethylamine (Et 3 N (1.40 mL, 10.0 mmol) was then added to the 0 • C mixture under N 2 .…”

An Investigation into Interactions between 1‐Butyl‐3‐methyl‐imidazolium Tetrafluoroborate Guest and Pillar[5]arene Hosts: An Experimental and Molecular Dynamics Approach

“…Inspired by the intriguing and fascinating structure of pillar [n]arene macrocycles, and the great potential they hold in the host-guest chemistry, we embarked on research in this field. [25] As a starting point, we were interested in investigating the host-guest chemistry of pillar [5]arenes with novel guests. Toward that end, we report, herein, formations of inclusion complexes of three synthesized pillar [5]arenes with an ionic liquid.…”