Acylation
Ammonia acylation converts acyl chlorides into amides.
- Reagents
- concentrated NH3
- Conditions
- room temperature
- Reaction class
- acylation
- Equation
- R-COCl + 2NH3 -> R-CONH2 + NH4Cl
Overview
Ammonia acylation converts acyl chlorides into amides.
Transformation
- Equation
- R-COCl + 2NH3 -> R-CONH2 + NH4Cl
- Reagents
- concentrated NH3
- Environment
- room temperature
- Reaction class
- acylation
- Mechanism
- nucleophilic acyl substitution
- Evidence level
- textbook core
Scope and limitations
- Scope
- Acyl chlorides react with ammonia to form primary amides.
- Limitations
- This route records ammonia acylation of acyl chlorides; hydrogen chloride is trapped by excess ammonia to give ammonium chloride.
Related reactions
- Chlorination: Carboxylic acids → Acyl chlorides
PCl5 converts carboxylic acids into acyl chlorides.
- Chlorination with thionyl chloride: Carboxylic acids → Acyl chlorides
Thionyl chloride converts carboxylic acids into acyl chlorides with sulfur dioxide and hydrogen chloride as by-products.
- Hydrolysis: Acyl chlorides → Carboxylic acids
Water hydrolyses acyl chlorides to carboxylic acids, releasing hydrogen chloride.
- Acylation: Acyl chlorides → Esters
Alcohol acylation converts acyl chlorides into esters.
- Acylation: Acyl chlorides → N-substituted amides
Amine acylation converts acyl chlorides into N-substituted amides.
- Anhydride ammonolysis: Acid anhydrides → Amides
Ammonia attacks the anhydride carbonyl to form a tetrahedral intermediate. Carboxylate departure and proton transfer give an amide; excess ammonia also converts the acid co-product into ammonium carboxylate.
References
- Organic Chemistry: Chemistry of Acid HalidesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports acid-halide preparation with thionyl chloride and nucleophilic acyl substitution chemistry, including tetrahedral intermediates, hydrolysis, alcoholysis and amine acylation at acid chlorides.