Nitroso Compound Synthesis via Tertiary Alcohol Mediation

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Solution Overview

Problem

Current methods for producing nitroso compounds and quinoxaline compounds require extreme low temperatures, making them industrially impractical due to the need for specialized facilities and using less available raw materials, such as 2,6-dichloronitrobenzene and ketomalonic acid diester, which are costly and inefficient.

Innovation Solution

A method involving the reaction of a nitro compound with an aniline compound using a tertiary alcohol and a base, such as sodium hydride or lithium amide, at temperatures ranging from -5°C to 80°C, reducing the need for extreme low temperatures and utilizing more readily available materials like 2-chloronitrobenzene and p-anisidine.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If extreme low temperature conditions (-70°C to 0°C) are used for producing nitroso compounds, then high yield can be achieved, but specialized production facilities are required and the method becomes industrially impractical

Engineering Contradiction:

ImproveyieldVSAvoidindustrial practicality

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The invention changes the temperature parameter from extreme low temperature (-70°C to 0°C) to a broader, more practical range (-50°C to room temperature), thereby maintaining high yield while enabling industrial practicality through the use of readily available materials and simplified production facilities

Inventive Principle:

Principle #35Parameter changes

2Productivity

If 2,6-dichloronitrobenzene and ketomalonic acid diester are used as raw materials, then quinoxaline compounds can be produced, but these materials are less available and more costly

Engineering Contradiction:

Improveproduction efficiencyVSAvoidraw material availability

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The invention replaces expensive and less available raw materials (2,6-dichloronitrobenzene and ketomalonic acid diester) with cheaper and more readily available alternatives (2-chloronitrobenzene and p-anisidine), thereby improving raw material availability and reducing production costs while maintaining production efficiency

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

3Productivity

If multiple steps (three steps) are used to produce quinoxaline compounds from 2,6-dichloronitrobenzene, then the reaction can proceed, but the production process becomes complex and less efficient

Engineering Contradiction:

Improvereaction completionVSAvoidnumber of steps

Core Design Contradiction:

ProductivityVSDevice complexity

Solution Approach 1:

The invention merges multiple reaction steps into a simplified process by using 2-chloronitrobenzene and p-anisidine as starting materials, which directly undergo reaction to form the desired nitroso compound and subsequently the quinoxaline compound, thereby reducing the number of steps from three to two while maintaining reaction completion

Inventive Principle:

Principle #5Merging (Combining)

4Productivity

If 2 equivalents to 3 equivalents of p-anisidine are used based on 2-chloronitrobenzene, then the reaction can proceed, but the amount of p-anisidine consumed increases production costs

Engineering Contradiction:

Improvereaction completionVSAvoidp-anisidine consumption

Core Design Contradiction:

ProductivityVSLoss of substance

Solution Approach 1:

The invention optimizes the stoichiometric ratio of reactants by using a controlled amount of p-anisidine relative to 2-chloronitrobenzene, avoiding excessive consumption (2-3 equivalents) while ensuring complete reaction, thereby reducing material loss and production costs while maintaining reaction completion

Inventive Principle:

Principle #16Partial or excessive action

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

This method allows for the production of nitroso and quinoxaline compounds in a more industrially viable, economical, and environmentally friendly manner by eliminating the need for extreme low temperatures and using more accessible raw materials, thereby improving yield and reducing production costs.

Implementation Method 1

reacting a compound of a formula (1) with a compound of a formula (2) by using a tertiary alcohol and a base

Methodology Applied

Scientific EffectDeprotonation:

Implementation Method 2

The reaction of the compound of the formula (1) with the compound of the formula (2)

Methodology Applied

Scientific EffectNucleophilic substitution:

Implementation Method 3

reacting a compound of a formula (1) with a compound of a formula (2) by using a tertiary alcohol and a base

Methodology Applied

Scientific EffectChemical transformation:

Data Source

PatentUS12122755B2Methods for producing nitroso compound and quinoxaline compound

Publication Date: 2024.10.22 KUMIAI CHEM IND CO LTD

AI summary

A method for producing a compound of a formula (3), including reacting a compound of a formula (1) with a compound of a formula (2) by using a tertiary alcohol and a base:where R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently a hydrogen atom, a halogen atom, a (C1-C4)alkyl, or a (C1-C4)alkoxy, the amount of the base used is 2.0-4.0 equivalents per 1 equivalent of the compound of formula (2), the amount of the tertiary alcohol used is 0.3-2.5 equivalents per 1 equivalent of the compound of formula (2), the base is a plurality of compounds comprising a lithium-containing base as a first compound, and a second compound selected from the group consisting of alkali metal hydrides, alkali metal amides, alkoxides, alkyl metals, alkali metals, and organic bases, and the reaction is performed in the presence of an aromatic hydrocarbon solvent.