5330-63-2

Usage

InChI:InChI=1/C11H14ClNO2/c1-11(2,3)15-10(14)13-9-6-4-5-8(12)7-9/h4-7H,1-3H3,(H,13,14)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 108-42-9 3-chloro-aniline 
• 1239374-13-0 tert-butyl 3-chlorophenyl(3-perfluorooctylpropoxy)carbamate 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 4248-19-5 tert-butyl carbazate 
• 108-90-7 chlorobenzene 
• 110-05-4 di-tert-butyl peroxide 
• 32686-54-7 m-chlorophenyl isocyanide 

Downstream Products

• 652153-34-9 (3-chlorophenyl)-(4-chloro-[1,3,5]triazin-2-yl)carbamic acid tert-butyl ester 
• 3422-01-3 tert-butyl phenylcarbamate 
• 1384313-08-9 N-(tert-butoxycarbonyl)-N-methyl-3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 1384313-14-7 C₁₇H₂₄⁽²⁾HBClNO₄ 
• 1384313-16-9 C₁₇H₂₄⁽²⁾HBClNO₄ 
• 1186637-28-4 N-(tert-butoxycarbonyl)-5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 1384312-60-0 N-(tert-butoxycarbonyl)-5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 1384312-79-1 N-(tert-butoxycarbonyl)-N-methyl-3-chloroaniline 
• 108-42-9 3-chloro-aniline 
• 18109-43-8 N-(3-chlorophenyl)-2-phenylacetamide 
• 7006-52-2 3-chloro-N-methylaniline 
• 39165-01-0 N-(3-chlorophenyl)-2-oxo-2-phenylacetamide 
• 652153-43-0 [4-(2-{tert-butoxycarbonyl-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-amino}-pyridin-4-yl)-[1,3,5]triazin-2-yl]-(3-chloro-phenyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Mild deprotection of the: N-tert -butyloxycarbonyl (N -Boc) group using oxalyl chloride

We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1-4 h with yields up to 90percent. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy. This journal is

Anionic Fries rearrangement of aryl carbonates. A facile route to ortho-hydroxy esters

Aryl carbonates react with LDA or LiTMP to produce ortho-hydroxy esters.

PRODUCTION METHOD FOR AMIDATE COMPOUND

A method for producing an amidate compound represented by Formula (3), comprising reacting a urethane compound represented by Formula (1) with a carboxylate compound represented by Formula (2): (in the formulas, A, n, R1, R2, R3, R4, R5, R6, X, and a are as described in the Description).

Amidate compound, catalyst for polyurethane production, and method for producing polyurethane resin

Provided is an amidate compound represented by the formula (1): wherein A is a substituted or unsubstituted hydrocarbon group, n is an integer of 1 or more, and D is a nitrogen-containing organic group represented by the formula (2): wherein R1, R2, and R3 are the same or different, and are each a hydrocarbon group that may contain a heteroatom; some or all of R1, R2, and R3 may be bonded together to form a ring structure; X is a nitrogen atom, an oxygen atom, or a sulfur atom; and a is 0 or 1, wherein a is 1 when X is a nitrogen atom, and a is 0 when X is an oxygen atom or a sulfur atom.

Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent

A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N-arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C?C and C?O bond-forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used. (Figure presented.).

Teaching Old Compounds New Tricks: DDQ-Photocatalyzed C?H Amination of Arenes with Carbamates, Urea, and N-Heterocycles

The C?H amination of benzene derivatives was achieved using DDQ as photocatalyst and BocNH2 as the amine source under aerobic conditions and visible light irradiation. Electron-deficient and electron-rich benzenes react as substrates with moderate to good product yields. The amine scope of the reaction comprises Boc-amine, carbamates, pyrazoles, sulfonimides and urea. Preliminary mechanistic investigations indicate arene oxidation by the triplet of DDQ to radical cations with different electrophilicity and a charge transfer complex between the amine and DDQ as intermediate of the reaction.

Preparation, characterization and application of 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl) as an efficient dicationic ionic catalyst for the N-Boc protection of amines

In this work, 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl), as a novel Br?nsted acidic ionic catalyst is synthesized and characterized using a series of techniques including FT-IR, TGA, DTA, SEM, pH analysis and Hammett acidity function. This substance can significantly catalyze the N-Boc protection of amines without solvent interference at room temperature. The advantages of this manner are chemoselectivity, short reaction times, suitable yields, excellent yields of the products, without solvent interference and ease of preparation as well as reusability of the catalyst.

Sustainable and chemoselective N-Boc protection of amines in biodegradable deep eutectic solvent

Abstract: A green and practical approach for the chemoselective N-tert-butyloxycarbonylation of structurally diverse amines with di-tert-butyl dicarbonate (Boc2O) is described. Selective N-Boc protection was achieved in excellent yields in urea-choline chloride deep eutectic solvent (DES) as the most promising environmentally benign and cost-effective solvent under mild reaction condition. DES can protect various aromatic and aliphatic amines using Boc2O in good to excellent yields in short reaction times without any side products. Graphical abstract: [Figure not available: see fulltext.].

Palladium-Catalyzed Decarboxylative Synthesis of Arylamines

A novel approach has been developed for the synthesis of arylamines via the palladium-catalyzed intramolecular decarboxylative coupling (IDC) of aroyloxycarbamates, obtained in situ by reacting aryl carboxylic acids with hydroxycarbamates. The reaction offers facile access to structurally diverse arylamines with the site-specific formation of the C(sp2)-N bond under mild conditions.

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles

Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.