Direct Cyclic Imide Synthesis Without Acid Anhydride Intermediates

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Solution Overview

Problem

Existing methods for producing cyclic imide compounds with an azaperylene skeleton suffer from low yield and purity, particularly due to the poor solubility and handling issues of acid anhydride intermediates.

Innovation Solution

A novel production method involving direct reaction of a compound represented by formula (1) with amine compounds to synthesize a cyclic imide compound without using acid anhydride intermediates, including steps of reaction, protecting group removal, and purification to achieve high yield and purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If existing methods using acid anhydride intermediates are employed, then the production process can be established, but the yield and purity are low due to poor solubility and handling issues

Engineering Contradiction:
ImproveyieldVSAvoidhandling of acid anhydride intermediates
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The invention extracts and eliminates the problematic acid anhydride intermediate from the synthesis pathway. By using a novel condensing agent that directly facilitates cyclization without forming isolable acid anhydride intermediates, the method removes the source of solubility and handling problems while maintaining production capability.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention introduces a novel condensing agent as an intermediary substance that mediates the reaction between the starting material and amine compound. This intermediary enables the formation of cyclic imide compounds with high yield and purity by facilitating the condensation reaction without requiring the formation of difficult-to-handle acid anhydride intermediates.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If existing methods are used, then the synthesis pathway is established, but the purity of the cyclic imide compound is low

Engineering Contradiction:
ImprovepurityVSAvoidsynthesis process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The condensing agent acts as a mediator that controls the reaction to proceed cleanly with high selectivity. This intermediary substance enables the direct conversion of starting materials to high-purity cyclic imide compounds, eliminating the need for multiple purification steps and reducing overall process complexity.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention changes the reaction parameters by using a novel condensing agent that operates under optimized conditions. This parameter change enables the reaction to proceed with high selectivity and purity, avoiding side reactions that would require complex purification processes.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If acid anhydride intermediates are used, then the reaction pathway is defined, but the solubility and handling become problematic

Engineering Contradiction:
ImprovesolubilityVSAvoidcomposition stability
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The invention removes the acid anhydride intermediate from the reaction pathway, eliminating the solubility and handling problems associated with this intermediate. The novel condensing agent enables direct cyclization without forming the problematic intermediate, while maintaining composition stability through controlled reaction conditions.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The condensing agent functions as a temporary, consumable substance that facilitates the reaction and is then removed or decomposed. This disposable intermediary enables the reaction to proceed under conditions that ensure solubility and ease of handling, without requiring the isolation or storage of unstable intermediates.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The method enables the production of cyclic imide compounds with improved yield and purity, addressing the limitations of previous techniques.

Implementation Method 1

reacting a compound represented by formula (1) with at least one amine compound to obtain a cyclic imide compound

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS12410169B2Method for producing cyclic imide compound, composition, and compound
Publication Date: 2025.09.09 FUJIFILM CORP
  • US12410169B2 patent drawing
  • US12410169B2 patent drawing
  • US12410169B2 patent drawing

AI summary

A first object of the present invention is to provide a method for producing a cyclic imide compound with high yield and high purity. A second object of the present invention is to provide a composition that can be used in the method for producing a cyclic imide compound with high yield and high purity. A third object of the present invention is to provide an intermediate compound that can be used in the method for producing a cyclic imide compound with high yield and high purity. The method for producing a cyclic imide compound according to the present invention includes reacting a compound represented by formula (1) below with at least one amine compound to obtain a compound represented by formula (2) below.