CN105001175A - 一种2-芳基-2-恶唑啉的制备方法 - Google Patents

一种2-芳基-2-恶唑啉的制备方法 Download PDF

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CN105001175A
CN105001175A CN201510301648.7A CN201510301648A CN105001175A CN 105001175 A CN105001175 A CN 105001175A CN 201510301648 A CN201510301648 A CN 201510301648A CN 105001175 A CN105001175 A CN 105001175A
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aryl
oxazoline
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ethylene dichloride
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CN105001175B (zh
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李刚
杨素玲
王志勇
吴汉夔
何其戈
韩晴晴
马星星
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Anyang Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

本发明公开了一种芳基-2-恶唑啉的制备方法，属于化学领域。该方法采用芳基酰胺化合物与1，2-二氯乙烷反应合成，所述的合成反应在碱性条件下进行。本发明使用相对廉价的1，2-二氯乙烷取代了价格较高的氨基乙醇为原料，合成反应的经济性得到提高，在保证产品质量的情况下增加了产品的成本优势。

Description

一种2-芳基-2-恶唑啉的制备方法
技术领域
本发明涉及一种恶唑啉的制备方法，特别涉及一种2-芳基-2-恶唑啉的制备方法，属于化学领域。
背景技术
2-恶唑啉及其衍生物是一类重要的有机化合物，是合成很多染料、医药、农药、涂料以及新材料等关键中间体。发展和探索有效且廉价地制备2-恶唑啉衍生物新方法一直是个研究热点。截至目前为止，人类已发展的合成2-芳基-2-恶唑啉衍生物的主要方法为芳基羧酸衍生物（芳基酸、芳基腈、芳基羧酸酯）以及芳基甲醛和芳基甲醇等与氨基乙醇在不同条件下反应，反应式如下：
这些方法产率较好，且很多已被广泛应用于实验室和工业合成中。可是这些方法中所使用的氨基乙醇价格偏高，因此在2-芳基-2-恶唑啉及其衍生物的合成上需要一种原料成本更加低廉的新合成工艺。
发明内容
本发明的目的在于克服目前上述的合成原料成本较高的缺陷，提供一种原料易得、更为经济的2-芳基-2-恶唑啉的制备方法。
为实现本发明的目的，本发明所采用的技术方案为：一种2-芳基-2-恶唑啉的制备方法，所述的2-芳基-2-恶唑啉具有（Ⅲ）式的结构，所述的制备方法采用芳基酰胺化合物与1，2-二氯乙烷反应合成，所述的合成反应在碱性条件下进行，所述的芳基酰胺化合物式为式（Ⅰ）所示的结构，1，2-二氯乙烷如式（Ⅱ）所示，反应式如下：
其中Ar为：萘基或苯基；带有硝基或甲氧基或甲基或氯或氟的萘基；带有硝基或甲氧基或甲基或氯或氟的苯基，进一步的，所述的合成反应采用将芳基酰胺、二氯乙烷、碱直接加入反应装置中，搅拌加热温度至135℃-145℃，反应24小时，分离产物得到芳基胺，进一步的，所述的碱为碳酸铯或碳酸钠或磷酸钾，碱的摩尔用量为芳基酰胺摩尔数的2-3倍。
 本发明所具有的积极有益技术效果在于：本发明的原料易得，反应条件简单，使用相对廉价的1，2-二氯乙烷取代了价格较高的氨基乙醇为原料，合成反应的经济性得到提高，在保证产品质量的情况下增加了产品的成本优势。
具体实施方式
为了更充分的解释本发明的实施，提供本发明的实施实例，这些实施实例仅仅是对本发明的阐述，不限制本发明的范围。
实施例1：
在20mL耐压反应管中加入121mg(1mmol)苯甲酰胺，1mL 1，2-二氯乙烷，210mg（2mmol）碳酸钠，密封，加热到140℃反应，搅拌24小时，反应后，柱色谱分离，得目标产物51mg，回收原料苯甲酰胺73mg及1，2-二氯乙烷。基于转化原料的产率为89%。回收的苯甲酰胺和1，2-二氯乙烷进一步利用。
实施例2：
在20mL耐压反应管中加入135mg(1mmol)4-甲基苯甲酰胺，1mL 1，2-二氯乙烷，210mg（2mmol）碳酸钠，密封，加热到140℃反应，搅拌24小时，反应后，柱色谱分离，得目标产物64mg，回收原料4-甲基苯甲酰胺73mg及1，2-二氯乙烷。基于转化原料的产率为87%。回收的4-甲基苯甲酰胺和1，2-二氯乙烷进一步利用。
 实施例3：
在20mL耐压反应管中加入171mg(1mmol)1-萘甲酰胺，1mL 1，2-二氯乙烷，210mg（2mmol）碳酸钠，密封，加热到140℃反应，搅拌24小时，反应后，柱色谱分离，得目标产物63mg，回收原料苯甲酰胺103mg及1，2-二氯乙烷。基于转化原料的产率为80%。回收的苯甲酰胺和1，2-二氯乙烷进一步利用。
 实施例4：
在20mL耐压反应管中加入121mg(1mmol)苯甲酰胺，1mL 1，2-二氯乙烷，751mg（2mmol）碳酸铯，密封，加热到140℃反应，搅拌24小时，反应后，柱色谱分离，得目标产物54mg，回收原料苯甲酰胺71mg及1，2-二氯乙烷。基于转化原料的产率为91%。回收的苯甲酰胺和1，2-二氯乙烷进一步利用。
下表为采用本发明的技术方案合成的产物及对应的产率，产物后面对应的百分数为产率，
 
可以看出，本发明的技术方案的最高产率（基于转化原料）超过90%。
 在详细说明本发明的实施方式之后，熟悉该项技术的人士可清楚地了解，在不脱离上述申请专利范围与精神下可进行各种变化与修改，凡依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与修饰，均属于本发明技术方案的范围，且本发明亦不受限于说明书中所举实例的实施方式。

Claims (3)

1.一种2-芳基-2-恶唑啉的制备方法，所述的2-芳基-2-恶唑啉具有（Ⅲ）式的结构，其特征在于：所述的制备方法采用芳基酰胺化合物与1，2-二氯乙烷反应合成，所述的合成反应在碱性条件下进行，所述的芳基酰胺化合物式为式（Ⅰ）所示的结构，1，2-二氯乙烷如式（Ⅱ）所示，反应式如下：
其中Ar为：萘基或苯基；带有硝基或甲氧基或甲基或氯或氟的萘基；带有硝基或甲氧基或甲基或氯或氟的苯基。
2.根据权利要求1所述的一种2-芳基-2-恶唑啉的制备方法，其特征在于：所述的合成反应采用将芳基酰胺、二氯乙烷、碱直接加入反应装置中，搅拌加热温度至135℃-145℃，反应24小时，分离产物得到芳基胺。
3. 根据权利要求2所述的一种2-芳基-2-恶唑啉的制备方法，其特征在于：所述的碱为碳酸铯或碳酸钠或磷酸钾，碱的摩尔用量为芳基酰胺摩尔数的2-3倍。
CN201510301648.7A 2015-06-04 2015-06-04 一种2‑芳基‑2‑噁唑啉的制备方法 Expired - Fee Related CN105001175B (zh)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022018651A3 (en) * 2020-07-21 2022-03-03 University Of Kwazulu-Natal Synthesis of heterocyclic compounds from carboxamide and carboxamide derivatives with haloalkanols

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005113522A1 (en) * 2004-05-07 2005-12-01 Janssen Pharmaceutica, N.V. Azole carboxamide inhibitors of bacterial type iii protein secretion systems

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005113522A1 (en) * 2004-05-07 2005-12-01 Janssen Pharmaceutica, N.V. Azole carboxamide inhibitors of bacterial type iii protein secretion systems

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
何晓东: "2-噁唑啉化合物的合成及应用", 《四川化工与腐蚀控制》 *
李元杰: "2-噁唑啉化合物的合成及其在聚合物中的应用", 《塑料助剂》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022018651A3 (en) * 2020-07-21 2022-03-03 University Of Kwazulu-Natal Synthesis of heterocyclic compounds from carboxamide and carboxamide derivatives with haloalkanols

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