Related Experiment Video
Updated: Sep 27, 2025
10:42
Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
9.9K
Method for Preparing N-Tosylhydrazonyl Chlorides
Qian Zhang1, Siyu Zhang1, Meng Tang1
1School of Pharmacy, Lanzhou University, Lanzhou 730000, P. R. China.
The Journal of Organic Chemistry
|April 13, 2022
Summary
A new, efficient method was developed to synthesize N-tosylhydrazonyl chlorides. This versatile reaction works for various substrates and substituents, enabling the preparation of novel N-tosylhydrazonyl chlorides.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- N-tosylhydrazonyl chlorides are important synthetic intermediates.
- Existing methods for their preparation can be inefficient or limited in scope.
Purpose of the Study:
- To develop a facile and efficient synthetic method for N-tosylhydrazonyl chlorides.
- To explore the general applicability and substituent compatibility of the new method.
Main Methods:
- A novel reaction pathway was employed for the synthesis.
- The reaction conditions were optimized for efficiency and yield.
Main Results:
- A facile and efficient method for preparing N-tosylhydrazonyl chlorides was successfully developed.
- The reaction demonstrated broad substrate scope and excellent compatibility with diverse substituents.
- A range of previously unreported N-tosylhydrazonyl chlorides were synthesized.
Conclusions:
- The developed method provides a valuable new route to N-tosylhydrazonyl chlorides.
- This approach is highly versatile and applicable to a wide array of organic synthesis challenges.
Related Concept Videos
01:12Preparation of Nitriles
2.2K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.2K
01:07Preparation of Acid Anhydrides
3.4K
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
3.4K
02:33Preparation and Reactions of Thiols
6.8K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.8K
01:24Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids
3.7K
Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
3.7K
01:19Preparation of Carboxylic Acids: Hydrolysis of Nitriles
4.8K
Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
4.8K
02:26Preparation and Reactions of Sulfides
5.2K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.2K