13053-81-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(Acetamido)thiophene is utilized as a building block for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Chemical Production:
2-(ACETAMIDO)THIOPHENE is also employed in the production of dyes, pigments, and other specialty chemicals, where its unique properties enhance the performance and characteristics of these products.
Used in Organic Synthesis:
Due to its versatile reactivity, 2-(Acetamido)thiophene is an important intermediate in organic synthesis, enabling the creation of a variety of complex organic molecules for diverse applications.

InChI:InChI=1/C6H7NOS/c1-5(8)7-6-3-2-4-9-6/h2-4H,1H3,(H,7,8)

Upstream product

• 2786-07-4 2-thienyl lithium 
• 60-35-5 acetamide 
• 609-40-5 2-nitrothiophene 
• 108-24-7 acetic anhydride 
• 6277-18-5 2-iodo-5-nitrothiophene 
• 92313-54-7 (E)-N-[1-(thiophen-2-yl)ethylidene]hydroxylamine 
• 1956-45-2 2-acetylthiophene oxime 
• 56267-50-6 tert-butyl (2-thienyl)carbamate 
• 103-69-5 N-ethyl-N-phenylamine 
• 5813-89-8 2-thiophenylcarboxamide 
• 616-46-6 thiophen-2-ylamine 
• 64-19-7 acetic acid 
• 4298-52-6 2-ethynyl-thiophene 
• 88-15-3 2-Acetylthiophene 

Downstream Products

• 72133-90-5 2-Acetamido-3-nitrothiophene 
• 51419-40-0 N-(5-nitrothiophen-2-yl)acetamide 
• 172896-61-6 N-methyl-N-(2-thienyl)thioacetamide 
• 172896-63-8 N-methyl-N-(2-thienyl)thiocarbamoylacetic acid 
• 1558047-03-2 N-(3-(4-methoxyphenyl)thiophen-2-yl)acetamide 
• 1558047-01-0 N-(3-phenylthiophen-2-yl)acetamide 
• 51249-08-2 2-acetamido-3,5-dinitrothiophene 

Relevant academic research and scientific papers

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition

Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides

A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.

MODIFIED PROTEINS AND PROTEIN DEGRADERS

Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.

Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

A zinc(II)-catalyzed single-step protocol for the Beckmann rearrangement using hydroxylamine-O-sulfonic acid (HOSA) as the nitrogen source in water was developed. This direct method efficiently produces secondary amides under open atmosphere in a pure form after basic aqueous workup. It isenvironmentally benign and operationally simple.

Direct synthesis of secondary amides from ketones through Beckmann rearrangement using O-(mesitylsulfonyl)hydroxylamine

The Beckmann rearrangement is a versatile method for the preparation of secondary amides from ketones via oxime intermediates and has been widely used in the synthesis of bioactive natural products and pharmaceuticals. Herein, we have developed a highly efficient direct method for the preparation of secondary amides and lactams from ketones using O-(mesitylsulfonyl)hydroxylamine (MSH). The reactions proceed rapidly at room temperature under mild condition without requiring any additive, and tolerate multiple functional groups. A simple aqueous work-up often furnished the products in excellent yield with high purity.

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.

Polystyrene-supported phosphine oxide-catalysed Beckmann rearrangement of ketoximes in 1,1,1,3,3,3-hexafluoro-2-propanol

A polystyrene-supported phosphine oxide-catalysed Beckmann rearrangement of ketoximes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) has been developed. Good substrate compatibility, mild reaction conditions, good yields as well as the reusability of the catalyst/solvent made this procedure more environmentally benign.

Synthesis of diverse libraries of carboxamides via chemoselective N-acylation of amines by carboxylic acids employing Br?nsted acidic IL [BMIM(SO3H)][OTf]

Chemoselective N-acylation of amines with carboxylic acids as acyl electrophiles and Br?nsted acidic IL [BMIM(SO3H)][OTf] as promoter is reported under both thermal and microwave irradiation to produce libraries of carboxamides in good to excellent yields after a simple workup. The protocol is compatible with structurally diverse 1° and 2° amines and works in the presence of sensitive functional groups such as thiols and phenols. The potential for recycling and reuse of the IL is also demonstrated.

Hydrative syntheses of amides from alkynes catalyzed by an Au(I) complex containing pyridyl-functionalized NHC ligand

An Au(I)-NHC complex [L1AuBr] (1) with appended pyridyl group on the ligand scaffold is synthesized and its catalytic efficacy for the direct synthesis of the amide from alkyne and sodium azide in acidic water is evaluated. Catalyst 1 readily converts a wide range of internal and terminal alkynes to the corresponding amides with low catalyst loading in TFA/DCE (2 mL, 1:1 v/v) at room temperature in short reaction time (2 h) and without the use of Ag(I) additive. A related catalyst that is devoid of the pyridyl fragment displays significantly lower activity illustrating the role of the promoter ligand for water activation. Mechanistic studies reveal an initial alkyne hydration to ketone followed by the Schmidt reaction to afford the amide.