Direct amidation of acids in a screw reactor for the continuous flow synthesis of amides

Atapalkar, Ranjit S.; Kulkarni, Amol A.

doi:10.1039/d3cc02402d

Cited by 4 publications

(2 citation statements)

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“…Some of these include mechanochemistry for carrying out the impossible reactions, 69 green metrics in mechanochemistry, 70 and mechanochemical rearrangement for organic synthesis with eco-friendly approach, especially for active pharmaceutical and complex natural products. 71 Recent reports on direct continuous mechanochemical solvent-free amidation 76,77 cover an important step toward solvent-free manufacturing.…”

Section: Future Directions/challengesmentioning

confidence: 99%

Batch and continuous flow mechanochemical synthesis of organic compounds including APIs

Atapalkar,

Kulkarni

2024

React. Chem. Eng.

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Section: Future Directions/challengesmentioning

confidence: 99%

Batch and continuous flow mechanochemical synthesis of organic compounds including APIs

Atapalkar,

Kulkarni

2024

React. Chem. Eng.

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“…Usually, N 1 on the arylhydrazines typically undergo substitution reactions with σ-electrophile halides and analogues under strong alkali conditions, or carbon–nitrogen bond coupling reactions by transition metals, resulting in N 1 -substituted arylhydrazines (Scheme , eq a). N 2 of arylhydrazines always react with π-electrophile carbonyl compounds to afford imines or amides (Scheme , eq b) . Obviously, a general method that is applicable to achieving selective N -functionalization of arylhydrazines under the same reaction was lacking.…”

Section: Introductionmentioning

confidence: 99%

Selective N-functionalization of Arylhydrazines with Primary Alcohols and Acids under PPh₃/DDQ System

Shu,

Yu,

et al. 2024

J. Org. Chem.

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We present a PPh3/DDQ-mediated regiospecific selective N-functionalization of arylhydrazines with primary benzylic alcohols and aryl carboxylic acids for the synthesis of N 1-benzyl arylhydrazines and N 2-acyl arylhydrazines, respectively. This metal- and base-free approach features very short reaction times (about 10 min), broad substrate scope, good functional group tolerance, and mild reaction conditions. Furthermore, N 1-benzlated products have also been successfully applied to the concise synthesis of N-substituted indoles and anticancer drug MDM2 inhibitor.

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Solvent Minimized Synthesis of Amides by Reactive Extrusion

Bolt,

Smallman,

Leitch

et al. 2024

Angewandte Chemie

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Herein, we report on the translation of a small scale ball‐milled amidation protocol into a large scale continuous reactive extrusion process. Critical components to the successful translation were: a) understanding how the different operating parameters of a twin‐screw extruder should be harnessed to control prolonged continuous operation, and b) consideration of the physical form of the input materials. The amidation reaction is applied to 36 amides spanning a variety of physical form combinations (liquid‐liquid, solid–liquid and solid‐solid). Following this learning process, we have developed an understanding for the translation of each physical form combination and demonstrated a 7‐hour reactive extrusion process for the synthesis of an amide on 500 gram scale (1.3 mols of product).

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Direct amidation of acids in a screw reactor for the continuous flow synthesis of amides

Abstract: A simple and efficient solvent-free protocol for continuous flow synthesis of amides at room temperature is developed using easily available starting materials. N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC.HCl) was used as the reagent...

Cited by 4 publications

References 40 publications

Batch and continuous flow mechanochemical synthesis of organic compounds including APIs

Batch and continuous flow mechanochemical synthesis of organic compounds including APIs

Selective N-functionalization of Arylhydrazines with Primary Alcohols and Acids under PPh₃/DDQ System

Solvent Minimized Synthesis of Amides by Reactive Extrusion

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Direct amidation of acids in a screw reactor for the continuous flow synthesis of amides

Abstract: A simple and efficient solvent-free protocol for continuous flow synthesis of amides at room temperature is developed using easily available starting materials. N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC.HCl) was used as the reagent...

Cited by 4 publications

References 40 publications

Batch and continuous flow mechanochemical synthesis of organic compounds including APIs

Batch and continuous flow mechanochemical synthesis of organic compounds including APIs

Selective N-functionalization of Arylhydrazines with Primary Alcohols and Acids under PPh3/DDQ System

Solvent Minimized Synthesis of Amides by Reactive Extrusion

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Product

Resources

About

Selective N-functionalization of Arylhydrazines with Primary Alcohols and Acids under PPh₃/DDQ System