65847-73-6

Basic information

• Product Name: N-(BENZOFURAN-2-YL)ACETAMIDE
• Synonyms: N-(BENZOFURAN-2-YL)ACETAMIDE
• CAS NO: 65847-73-6
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.18
• Mol File: 65847-73-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-(BENZOFURAN-2-YL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(BENZOFURAN-2-YL)ACETAMIDE(65847-73-6)
• EPA Substance Registry System: N-(BENZOFURAN-2-YL)ACETAMIDE(65847-73-6)

Safety Data

• Hazardous Substances Data: 65847-73-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-(Benzofuran-2-yl)acetamide is used as a building block in the synthesis of various compounds for pharmaceutical research. Its unique structure and properties make it a valuable component in the development of new drugs.
Used in Organic Synthesis:
N-(Benzofuran-2-yl)acetamide is used as a key intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds with diverse applications.
Used in the Development of Selective Serotonin Reuptake Inhibitors (SSRIs):
N-(Benzofuran-2-yl)acetamide is used as a potential therapeutic agent for the treatment of various medical conditions, particularly due to its activity as a selective serotonin reuptake inhibitor. This property makes it a promising candidate for the development of new SSRIs to treat conditions such as depression, anxiety, and other mood disorders.
Used in the Treatment of Various Medical Conditions:
Due to its potential pharmacological properties, N-(Benzofuran-2-yl)acetamide is being studied for its potential as a therapeutic agent for the treatment of various medical conditions. Its ability to act as a selective serotonin reuptake inhibitor makes it a valuable compound in the search for new treatments for mood disorders and other related conditions.

Upstream product

• 4846-21-3 O-phenylhydroxylamine 
• 64908-64-1 2-phenoxyisoindol-1,3-dione 
• 98-80-6 phenylboronic acid 
• 685-91-6 diethylacetamide 
• 5661-50-7 N-(phenoxy)acetamide 
• 181934-30-5 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one 
• 72583-88-1 N²-Phenylbenzo[b]furan-2-carboximidamide 
• 4265-16-1 2-formylbenzo[b]furan 
• 41717-32-2 benzofuran-2-carbonitrile 
• 350692-34-1 N¹-Acetyl-N¹-(benzo[b]furan-2-yl)-N²-phenylurea 

Relevant articles and documents

Synthesis of Benzofurans and Benzoxazoles through a [3,3]-Sigmatropic Rearrangement: O-NHAc as a Multitasking Functional Group

The synthesis of heterocycles relies heavily on diverse sigmatropic rearrangements triggered by the cleavage of X-Y (X, Y = C, O, N, S, I) bonds. However, a unified rearrangement approach for constructing heterocyclic libraries is highly desirable. Encouraged by computational analysis of [3,3]-sigmatropic rearrangements, we can now rapidly synthesize oxa-heterocycles by treating N-phenoxyacetamides (Ph-ONHAc) with compounds containing an sp-hybridized carbon. The generality of the process is illustrated by the late-stage diversification of natural products, including estrone and an approved drug. A combination of experimental and computational studies revealed that the reactions proceed through a facile Claisen-like [3,3]-sigmatropic rearrangement/annulation process.

N-Phenoxyamides as Multitasking Reagents: Base-Controlled Selective Construction of Benzofurans or Dihydrobenzofuro[2,3- d]oxazoles

An efficient method to selectively construct benzofuran and dihydrobenzofuro[2,3-d]oxazole derivatives has been successfully established by means of base-controlled cyclization of N-phenoxyamides with 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX). N-phenoxyamides as multitasking reagents have triggered two different cascade reaction sequences. This is the first example of using TIPS-EBX for the transformation of C(sp) to either C(sp2) or C(sp3) under metal-free conditions.

A 2 - aminobenzofuran preparation method of the compound

The invention belongs to the technical field of organic synthesis of novel 2 - aminobenzofuran preparation method of the compound. The method is: in - 30 °C conditions, in the reactor, adding substitution N - phenoxy amide and three (isopropyl silicon-based) ethynyl high-iodine compound and tetrabutyl ammonium fluoride, in the solvent after the completion of the reaction, using a rotary evaporator concentrated to get the crude product, the crude product using silica gel column chromatography separation to obtain the target product. The present invention provides 2 - aminobenzofuran synthetic method of the compound with scientific and reasonable, synthetic method is relatively simple, high yield of the compound, the product is easy to purification processing and the like. Its reaction equation is as follows:

The oxidative rearrangement of furan-2-carboximidamides: Preparation and properties of 2-acylaminofurans

Oxidation of furan-2-carboximidamides 8 by (dicarboxyiodo)benzenes gives N1-acyl-N1-(2-furyl)ureas 9 via rearrangement to a carbodiimide. Thermolysis of eleven ureas 9 gave the corresponding 2-acylaminofurans 10, which cannot be made from the free amines owing to their high instability. When oxidation of the corresponding benzo[b]furan derivatives 12 was investigated a new type of product was isolated, in addition to the expected ureas 14, and these were shown to be benzo[4,5]furo[2,3-d]pyrimidine derivatives 15. The mechanism of formation of these products must involve reaction of the carbodiimide intermediate with the amidine precursor and cyclisation of the resulting guanidine derivatives 19. The corresponding tetraphenylguanidine 21 was prepared and underwent thermal cyclisation but the quinazoline derivative formed 23 was shown to occur via an alternative cyclisation mechanism. The structures of cyclisation products 15 and 23 were confirmed by X-ray crystallography. N-(2-Furyl)acetamide 10a readily undergoes cycloaddition reactions with electron-deficient alkynes to give phenols after spontaneous ring opening. Observed regioselectivity is in agreement with the results of AM1 molecular orbital calculations. Reaction of the amide 10a with Lawesson's reagent gave the thioamide 26.