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Acetamidines are the starting materials of many entities, that find usage for compounds of biochemical activity manufacture. However, the free acetamidine base absorbs moisture from the atmosphere, decomposes at elevated temperature, and is converted into acetamidinium carbonate when stored in contact with air for short while at room temperature. So acetamidinium salts are preferred alternatives to acetamidines. Many synthetic routes for acetamidinium salts have been reviewed. Among the various acetamidinium salts available, acetamidinium chloride is the most commonly used salt of acetamidine, and prepared by the addition of ammonia to the intermediate imine ether after the mixing of acetonitrile and alcohol in the presence of hydrogen chloride. The main disadvantage of acetaminium chloride is its release of the free base in methanol in the presence of a methoxide, producing sodium chloride, which is partly soluble in methanol. This conversion is unfavourable in certain syntheses, and the complete removal is tedious.

Acetamidines are starting materials for many heterocycles such as imidazoles, pyrimidines, and triazinesentities, which in turn can be used to synthesize biochemically active that find usage for compounds of biochemical activity manufacture. However, the free acetamidine base is hygroscopic,absorbs moisture from the atmosphere, decomposes at elevated temperatures, and is converted into acetamidinium carbonate even upon short-term exposure when to stored in contact with air for short while at room temperature. Hence,So acetamidinium salts are preferred alternatives to acetamidines.

Many synthetic routes for to acetamidinium salts have been reviewed. Among the various acetamidinium salts available, acetamidinium chloride is the most commonly used salt of acetamidine., and It is usually prepared by mixing acetonitrile with an alcohol in the presence of hydrogen chloride, followed by the addition of ammonia to obtain the desired saltintermediate imine ether after the mixing of acetonitrile and alcohol in the presence of hydrogen chloride. The main disadvantage of acetamidinium chloride is that its release of the free base is releasedin methanol by the use of a methoxide, producing sodium chloride, which cannot be completely removed because of its is partial solubility partly soluble in methanol. This conversion is unfavourable forin certain syntheses, and the complete removal is tedious.

 

Source: Synthesis and properties of acetamidinium salts by Jalový Zdeněk, Matyáš Robert, Ottis Jan, Růžička Aleš, Šimůnek Petr, Polášek Miroslav, used under CC-BY 4.0

 

Acetamidines are the starting materials of many entities, that find usage for compounds of biochemical activity manufacture. However, the free acetamidine base absorbs moisture from the atmosphere, decomposes at elevated temperature, and is converted into acetamidinium carbonate when stored in contact with air for short while at room temperature. So acetamidinium salts are preferred alternatives to acetamidines. Many synthetic routes for acetamidinium salts have been reviewed. Among the various acetamidinium salts available, acetamidinium chloride is the most commonly used salt of acetamidine, and prepared by the addition of ammonia to the intermediate imine ether after the mixing of acetonitrile and alcohol in the presence of hydrogen chloride. The main disadvantage of acetaminium chloride is its release of the free base in methanol in the presence of a methoxide, producing sodium chloride, which is partly soluble in methanol. This conversion is unfavourable in certain syntheses, and the complete removal is tedious.

Acetamidines are the starting materials of many compoundsentities, that in turn can be used to prepare find usage for compounds withof biochemical activity manufacture. However, the free acetamidine base absorbs moisture from the atmosphere, decomposes at elevated temperatures, and is converted into acetamidinium carbonate when stored in contact with air for a short while period of time at room temperature. Hence,So acetamidinium salts are preferred alternatives to acetamidines. Many synthetic routes tofor acetamidinium salts  have been reviewed. Among the various acetamidinium salts available, acetamidinium chloride is the most commonly used salt of acetamidine;, and it is prepared by mixing acetonitrile with an alcohol in the presence of hydrogen chloride, followed by the addition of ammonia to the intermediate imine ether after the mixing of acetonitrile and alcohol in the presence of hydrogen chloride . The main disadvantage of acetamidinium chloride is that its release of the free base is released when the salt is dissolved in methanol in the presence of a methoxide, producing sodium chloride, which is partly soluble in methanol. This conversion is unfavourable in certain syntheses, and because the complete removal of sodium chloride is tedious.

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