Acylation co reactant
Amines are acylated by acyl chlorides to form N-substituted amides.
- Reagents
- acyl chloride
- Conditions
- room temperature
- Reaction class
- acylation
- Equation
- R-COCl + 2R'NH2 -> R-CONHR' + R'NH3Cl
Overview
Amines are acylated by acyl chlorides to form N-substituted amides.
Transformation
- Equation
- R-COCl + 2R'NH2 -> R-CONHR' + R'NH3Cl
- Reagents
- acyl chloride
- Environment
- room temperature
- Reaction class
- acylation
- Mechanism
- nucleophilic acyl substitution
- Evidence level
- textbook core
Scope and limitations
- Scope
- Primary or secondary amines react with acyl chlorides to form N-substituted amides.
- Limitations
- This record represents the amine reactant branch of acyl chloride aminolysis; amine substitution pattern and salt stoichiometry vary with substrate.
Related reactions
- Amination: Chloroalkanes → Amines
Ammonia substitutes chloride to form a primary amine; excess ammonia limits further alkylation.
- Amination: Bromoalkanes → Amines
Ammonia substitutes bromide to form a primary amine; excess ammonia limits further alkylation.
- Amination: Iodoalkanes → Amines
Ammonia substitutes iodide to form a primary amine; excess ammonia limits further alkylation.
- Alkylation: Amines → Quaternary ammonium compounds
Amines can be further alkylated to permanent cationic quaternary ammonium groups used in antimicrobial and ion-exchange materials.
- Reduction: Nitriles → Amines
Nitriles can be reduced to primary amines, separating the amine feedstock route from later amide or materials chemistry.
- Acylation: Acyl chlorides → N-substituted amides
Amine acylation converts acyl chlorides into N-substituted amides.
- Weak base equilibrium: Amines → Aqueous alkylammonium ions
Amines are weak bases in water and form alkylammonium and hydroxide ions.
- Salt formation: Amines → Amine salts
Amines react with acids to form alkylammonium salts.
- Copper(II) complex formation: Amines → Copper-amine complexes
Amines react with aqueous copper(II) ions and form a deep-blue complex in excess amine.
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.