10354-42-4

Basic information

• Product Name: 2-Thiophenecarboxamide,N-cyclohexyl-
• Synonyms: 2-Thiophenecarboxamide,N-cyclohexyl-;N-cyclohexyl-2-thiophenecarboxamide
• CAS NO: 10354-42-4
• Molecular Formula: C₁₁H₁₅NOS
• Molecular Weight: 209.3079
• Mol File: 10354-42-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Thiophenecarboxamide,N-cyclohexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiophenecarboxamide,N-cyclohexyl-(10354-42-4)
• EPA Substance Registry System: 2-Thiophenecarboxamide,N-cyclohexyl-(10354-42-4)

Safety Data

• Hazardous Substances Data: 10354-42-4(Hazardous Substances Data)

Upstream product

• 5271-67-0 2-Thiophenecarbonyl chloride 
• 108-91-8 cyclohexylamine 
• 527-72-0 2-thiophenylcarboxylic acid 
• 70584-30-4 N-cyclohexyl-3,5-dimethyl-1H-pyrazole-1-carboxamide 
• 5813-89-8 2-thiophenylcarboxamide 
• 110-82-7 cyclohexane 
• 3437-95-4 2-Iodothiophene 
• 931-53-3 Cyclohexyl isocyanide 
• 1003-09-4 2-bromothiophene 
• 96-43-5 2-thienyl chloride 
• 201230-82-2 carbon monoxide 
• 626-62-0 Cyclohexyl iodide 

Downstream Products

• 20851-07-4 2,3,5-triphenylthiophene 
• 98-03-3 thiophene-2-carbaldehyde 
• 926312-67-6 (E)-N-cyclohexyl-1-(thiophen-2-yl)methanimine 
• 51305-86-3 N-cyclohexylthiophen-2-ylmethylamine 
• 1003-31-2 thiophene-2-carbonitrile 

Relevant articles and documents

A catalyst system for the formation of amides by reaction of carboxylic acids with blocked isocyanates

A catalyst for the reaction of blocked isocyanates (blocking agent diisopropylamine and dimethyl pyrazole) and carboxylic acids was identified. Magnesium and in some instances calcium salts proved to be highly active as catalyst. This reaction gives amides in quantitative yield and excellent selectivity and is suitable for coating and general chemical purposes.

Integration of co2 reduction with subsequent carbonylation: Towards extending chemical utilization of co2

Currently, it still remains a challenge to amplify the spectrum of chemical fixation of CO2, although enormous progress has been achieved in this field. In view of the widespread applications of CO in a myriad of industrial carbonylation processes, an alternative strategy is proposed in which CO2 reduction to CO is combined with carbonylation with CO generated ex situ, which affords efficiently pharmaceutically and agrochemically attractive molecules. As such, CO2 in this study was efficiently reduced by triphenysilane using CsF to CO in a sealed two-chamber reactor. Subsequently, palladium-catalyzed aminocar-bonylation, carbonylative Sonogashira coupling of aryl iodides, and rhodium(I)-mediated Pauson–Khand-type reaction proceeded smoothly to yield amides, alkynones, and bicyclic cy-clopentenones, respectively. Furthermore, the formed alkynones can further be successfully converted to a series of heterocycles, for example, pyrazoles, 3a-hydroxyisoxazolo[3,2-a]isoindol-8-(3aH)-one derivatives and pyrimidines in moderate yields. The striking features of this protocol include operational simplicity, high efficiency, and relatively broad application scope, which represents an alternative avenue for CO2 transformation.

In situ generated Pd(0) nanoparticles stabilized by bis(aryl)acenaphthenequinone diimines as catalysts for aminocarbonylation reactions in water

Aminocarbonylation of aryl iodides with aromatic and aliphatic amines, leading to formation of the corresponding amides, was efficiently carried out in water under 1?atm of CO using palladium nanoparticles (Pd NPs) formed in situ from [PdCl2(Ar2-BIAN)] complexes. The role of Ar2-BIAN ligands in the stabilization of Pd NPs was evidenced. The nature of the catalytically active species was confirmed by poisoning experiments, which highlighted that the catalyst is actually in the form of Pd NPs rather than soluble palladium complexes. In the aminocarbonylation of iodobenzene with substituted anilines good yields of amides were obtained, although the activity was depleted by the presence of substituents in the ortho positions of the aniline. On the other hand, in the reaction with aliphatic amines α-ketoamides were formed in addition to the amides. The selectivity towards α-ketoamides was increased by increasing the CO pressure to 10?atm, at equimolar amounts of PhI and amine. Pd NPs were successfully recovered after the catalytic reaction and recycled in five subsequent runs with only a marginal loss of activity after the fourth cycle.

Synthesis of amides via copper-catalyzed amidation of aryl halides using isocyanides

An efficient method for intermolecular CC cross-coupling reactions between isocyanides and aryl halides, catalyzed by copper(I) oxide, is developed. This transformation serves as a direct method for the preparation of benzamides in aqueous DMSO, in moderate to good yields.

Copper-catalyzed intermolecular amidation and imidation of unactivated alkanes

We report a set of rare copper-catalyzed reactions of alkanes with simple amides, sulfonamides, and imides (i.e., benzamides, tosylamides, carbamates, and phthalimide) to form the corresponding N-alkyl products. The reactions lead to functionalization at secondary C-H bonds over tertiary C-H bonds and even occur at primary C-H bonds. [(phen)Cu(phth)] (1-phth) and [(phen)Cu(phth)2] (1-phth2), which are potential intermediates in the reaction, have been isolated and fully characterized. The stoichiometric reactions of 1-phth and 1-phth2 with alkanes, alkyl radicals, and radical probes were investigated to elucidate the mechanism of the amidation. The catalytic and stoichiometric reactions require both copper and tBuOOtBu for the generation of N-alkyl product. Neither 1-phth nor 1-phth2 reacted with excess cyclohexane at 100 C without tBuOOtBu. However, the reactions of 1-phth and 1-phth2 with tBuOOtBu afforded N-cyclohexylphthalimide (Cy-phth), N-methylphthalimide, and tert-butoxycyclohexane (Cy-OtBu) in approximate ratios of 70:20:30, respectively. Reactions with radical traps support the intermediacy of a tert-butoxy radical, which forms an alkyl radical intermediate. The intermediacy of an alkyl radical was evidenced by the catalytic reaction of cyclohexane with benzamide in the presence of CBr4, which formed exclusively bromocyclohexane. Furthermore, stoichiometric reactions of [(phen)Cu(phth)2] with tBuOOtBu and (Ph(Me)2CO) 2 at 100 C without cyclohexane afforded N-methylphthalimide (Me-phth) from β-Me scission of the alkoxy radicals to form a methyl radical. Separate reactions of cyclohexane and d12-cyclohexane with benzamide showed that the turnover-limiting step in the catalytic reaction is the C-H cleavage of cyclohexane by a tert-butoxy radical. These mechanistic data imply that the tert-butoxy radical reacts with the C-H bonds of alkanes, and the subsequent alkyl radical combines with 1-phth2 to form the corresponding N-alkyl imide product.

Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature

The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for S N2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with unactivated secondary (and hindered primary) alkyl bromides and iodides using a single set of comparatively simple and mild conditions: inexpensive CuI as the catalyst, no separate added ligand, and C-N bond formation at room temperature. The method is compatible with a variety of functional groups, such as an olefin, a carbamate, a thiophene, and a pyridine, and it has been applied to the synthesis of an opioid receptor antagonist. A range of mechanistic observations, including reactivity and stereochemical studies, are consistent with a coupling pathway that includes photoexcitation of a copper-amidate complex, followed by electron transfer to form an alkyl radical.

Controlled and chemoselective reduction of secondary amides

This communication describes a metal-free methodology involving an efficient and controlled reduction of secondary amides to imines, aldehydes, and amines in good to excellent yields under ambient pressure and temperature. The process includes a chemoselective activation of a secondary amide with triflic anhydride in the presence of 2-fluoropyridine. The electrophilic activated amide can then be reduced to the corresponding iminium using triethylsilane, a cheap, rather inert, and commercially available reagent. Imines can be isolated after a basic workup or readily transformed to the aldehydes following an acidic workup. The amine moiety can be accessed via a sequential reductive amination by the addition of silane and Hantzsch ester hydride in a one-pot reaction. Moreover, this reduction tolerates various functional groups that are usually reactive under reductive conditions and is very selective to secondary amides.

A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions

Acid bromides were prepared efficiently from carboxylic acids with readily available ethyl tribromoacetate and triphenylphosphine at room temperature under neutral conditions. The present process is applicable to the preparation of various acid bromides from aromatic and aliphatic carboxylic acids. Aromatic carboxylic acids were found to be more reactive than aliphatic carboxylic acids under reaction conditions.

Determination of aromaticity indices of thiophene and furan by nuclear magnetic resonance spectroscopic analysis of their anilides

A series of m- and p-substituted anilides of benzoic acid, 2-thienoic acid, and 2-furoic acid were prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shifts of proton and carbon signals of the acyl aromatic rings and the Hammett σ. Plots of the chemical shift values of the carbonyl carbons of the benzanilides against those of the 2-thienamides and 2-furamides gave an excellent correlation and the values of the slopes are 0.79 and 0.52, respectively, in dimethyl sulfoxide-d6. The slopes could be considered as a set of aromaticity index.

Facile Conversions of Carboxylic Acids into Amides, Esters, and Thioesters Using 1,1'-Oxalyldiimidazole and 1,1'-Oxalyldi(1,2,4-triazole)

Aliphatic, aromatic, and heteroaromatic carboxylic acids react with 1,1'-oxalyldiimidazole (1) or 1,1'-oxalyldi(1,2,4-triazole) (2) in acetonitrile for 40 min at 40 degC to give the corresponding 1-acylazole intermediates (11), which promptly undergo aminolysis and alcoholysis to form amides (13) including dipeptides (14), esters (16), and thioesters (19).These findings show that both 1 and 2 can be utilized as condensing reagents for the synthesis of carboxylic acid derivatives.Keywords --- 1,1'-oxalyldiimidazole; 1,1'-oxalyldi(1,2,4-triazole); 1,1'-carbonyldiimidazole; 1-acylazole; condensing reagent; amidation; esterification; dipeptide; aminolysis; alcoholysis