CN111606846A - 一种n`-三氟甲磺酰基n杂芳香胺类化合物及其制备方法 - Google Patents

一种n`-三氟甲磺酰基n杂芳香胺类化合物及其制备方法 Download PDF

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CN111606846A
CN111606846A CN202010395292.9A CN202010395292A CN111606846A CN 111606846 A CN111606846 A CN 111606846A CN 202010395292 A CN202010395292 A CN 202010395292A CN 111606846 A CN111606846 A CN 111606846A
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trifluoromethanesulfonyl
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唐建荣
鄢明
白呈超
谢文健
辛伟贤
陈新滋
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Guangzhou Liwen Technology Co ltd
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Abstract

本发明公开了一种N'‑三氟甲磺酰基N杂芳香胺类化合物及其制备方法，包括以下步骤：在惰性气体保护下，以N杂芳香基氨为原料，在无水非质子溶剂中，与2‑[N,N‑双(三氟甲烷烷磺酰)氨基]吡啶进行反应，高产率得到N'‑三氟甲磺酰基N杂芳香胺类化合物。本发明提供的制备方法具有工艺简单，底物选择广泛，产率高的特点。本发明所提供的技术工艺简单，底物选择广泛，后处理纯化方式简便有效，可高效、高产率、高纯度的得到N'‑三氟甲磺酰基N杂芳香胺类化合物。

Description

一种N'-三氟甲磺酰基N杂芳香胺类化合物及其制备方法
技术领域
本发明涉及化学合成制备技术领域，具体为一种N’-三氟甲磺酰基N杂芳香胺类化合物及其制备方法。
背景技术
锂离子电池广泛应用于各种电子产品上。功能性添加剂是锂离子电池电解液的重要组成部分，是使锂离子电池满足各种不同性能要求的一个技术关键。N'-三氟甲磺酰基N杂芳香胺类化合物作为一种潜在的优良锂离子电池电解液添加剂，高产率的得到高纯度的N'-三氟甲磺酰基N杂芳香胺类化合物显得至关重要。
三氟甲磺酰化反应在有机合成中是很常见的化学合成反应。对于N杂芳香基氨的三氟甲磺酰化反应，常用的三氟甲磺酰化试剂有三氟甲磺酰氟、三氟甲磺酰氯和三氟甲磺酸酐。
专利WO2014048480报道了以吡啶作碱，二氯甲烷作溶剂，2-氨基吡啶与三氟甲磺酸酐反应生成N‘-三氟甲磺酰基-2-氨基吡啶，产率只有16%-27%。
专利US3923811报道了以三乙胺为碱，三氟甲磺酰氟与2-氨基-4-甲基吡啶反应制得单取代的三氟甲磺酰胺产物。专利WO2004011443报道了以N,N-二异丙基乙基胺为碱，三氟甲磺酸酐与含嘧啶基的氨类底物反应，制得单取代的三氟甲磺酰胺产物，产率只有70%。以上制备方法，需要加入过量的碱去中和反应生成的酸，所以反应后有大量的盐生成，后处理繁琐，有机相需要水洗，碱洗，调PH值，再经柱层析或重结晶提纯。而且反应不可避免的有双三氟甲磺酰胺产物生成，所以反应产率低。
WO2005070903报道了在钯与膦配体的催化下，具有氯代1,3,5三嗪基团的底物与三氟甲磺酰胺反应。该制备方法只有单三氟甲磺酰基产物生成，但是产率低，且需要用到贵金属钯，反应条件苛刻，成本高。
发明内容
本发明的目的在于提供一种制备方法简单，底物选择广泛，产率高，后处理简单的N'-三氟甲磺酰基N杂芳香胺类化合物及其制备方法，以解决上述背景技术中提出的问题。
为实现上述目的，本发明提供如下技术方案：
一种N'-三氟甲磺酰基N杂芳香胺类化合物，N'-三氟甲磺酰基N杂芳香胺类化合物具有式的结构式如下：
Figure 327755DEST_PATH_IMAGE001
进一步地，式中n=0时，其中X1-X6各自独立地选自碳原子或氮原子且X1-X6至少有一个为氮原子；R1为N杂芳香环上碳原子上所连N'-三氟甲磺酰基（
Figure 548652DEST_PATH_IMAGE002
），Rx为N杂芳香环上所连单个或多个Cl、Br、I、F、三氟甲基、C2-C8氟氢碳链、烷氧基、C1-C18直链或支链烷基。
进一步地，式中X1-X6所组成的N杂芳香基团为：吡啶，嘧啶，哒嗪，吡嗪，1,3,5-三嗪中的一种，但不只限于以上N杂芳香基团。
进一步地，式中n=1,2,3,4时， Xn基团分别为三元，四元，五元，六元环，R’x为Xn环上所连单个或多个Cl、Br、I、F、三氟甲基、C2-C8氟氢碳链、烷氧基、C1-C18直链或支链烷基。
进一步地，Xn基团为全碳或N杂三元，四元，五元，六元环。
本发明提供另一种技术方案：一种N’-三氟甲磺酰基N杂芳香胺类化合物及其制备方法，包括以下步骤：
在惰性气体保护下，反应温度为30-100℃，以N杂芳香基氨为原料，在无水非质子溶剂中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶进行反应，高产率得到N'-三氟甲磺酰基N杂芳香胺类化合物。
进一步地，N杂芳香基氨与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶的摩尔比为1-1.2:1。
进一步地，所用非质子溶剂包括酮类、醚类、苯类、腈类、卤代烷类、酯类和碳酸酯类，其中酮类选自丙酮、丁酮、甲基乙基酮、甲基叔丁基酮或甲基吡咯烷酮中的一种或多种的组合；醚类选自乙醚、叔丁基甲醚、丙醚、丁醚、异丁醚、四氢呋喃、二氧六环或乙二醇二甲醚中的一种或多种的组合；苯类选自苯、甲苯、二甲苯或三甲苯中的一种或多种的组合；腈类选自乙腈、丙腈、异丙腈中的一种或多种的组合；卤代烷类选自二氯甲烷、氯仿、四氯化碳中的一种或多种的组合；酯类选自乙酸乙酯、乙酸丙酯、乙酸异丙酯、乙酸丁酯或乙酸异丁酯中的一种或多种的组合；碳酸酯类选自碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、碳酸乙烯酯或碳酸丙烯酯中的一种或多种的组合；但不仅限于上述的溶剂。
与现有技术相比，本发明的有益效果是：
本发明N'-三氟甲磺酰基N杂芳香胺类化合物及其制备方法，在惰性气体保护下，以N杂芳香基氨为原料，在无水非质子溶剂中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶进行反应，高产率得到N'-三氟甲磺酰基N杂芳香胺类化合物，本发明所提供的技术工艺简单，底物选择广泛，后处理纯化方式简便有效，可高效、高产率、高纯度的得到N'-三氟甲磺酰基N杂芳香胺类化合物。
具体实施方式
以下将详细说明本发明实施例，然而，本发明实施例并不以此为限。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例1
N'-三氟甲磺酰基N杂芳香胺类化合物具有式的结构式如下：
式中n=0时，其中X1-X6各自独立地选自碳原子或氮原子且X1-X6至少有一个为氮原子；R1为N杂芳香环上碳原子上所连N'-三氟甲磺酰基（），Rx为N杂芳香环上所连单个或多个Cl、Br、I、F、三氟甲基、C2-C8氟氢碳链、烷氧基、C1-C18直链或支链烷基。
式中X1-X6所组成的N杂芳香基团为：吡啶，嘧啶，哒嗪，吡嗪，1,3,5-三嗪中的一种，但不只限于以上N杂芳香基团。
式中n=1,2,3,4时， Xn基团分别为三元，四元，五元，六元环。R’x为Xn环上所连单个或多个Cl、Br、I、F、三氟甲基、C2-C8氟氢碳链、烷氧基、C1-C18直链或支链烷基。
Xn基团为全碳或N杂三元，四元，五元，六元环。
氮气保护下，在100ml圆底烧瓶中加入2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(3.58g,0.01mol)与2-氨基吡啶（0.94g,0.01mol），50ml乙腈，磁力搅拌下，65℃反应4h，反应完全，减压旋干反应溶剂，得N, -三氟甲磺酰基-2-氨基吡啶粗品4.52g，粗产率为100%；再用乙醇重结晶得N, -三氟甲磺酰基-2-氨基吡啶3.84g，收率85%，纯度为99.9%。
实施例2
在惰性气体保护下，反应温度为40℃，以2-氨基-6-溴吡啶（M=173.01）（4.54g，26.25mmol）为原料，在250mL二氯甲烷中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(8.95g,25.00mmol)进行交换反应，TLC跟踪反应。反应完毕，减压旋干反应溶液，再经柱层析提纯（洗脱剂为V石油醚：V乙酸乙酯=10:1），高产率的得到2-N’单三氟甲磺酰胺基-6-溴吡啶7.02g，产率为92%，纯度为99.9%。
实施例3
在惰性气体保护下，反应温度为60℃，以2-胺基4-甲基嘧啶(2.86g,26.25mmol)为原料，在100mL乙腈中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(8.95g,25.00mmol)进行交换反应，TLC跟踪反应。反应完毕，减压旋干反应溶液，再经柱层析提纯，高产率的得到2-N’单三氟甲磺酰胺基-4-甲基嘧啶5.43g，产率为90%，纯度为99.9%。
实施例4
在惰性气体保护下，反应温度为60℃，以2-胺基-1,3,5-三嗪(2.64g,27.50mmol)为原料，在100mL乙腈中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(8.95g,25.00mmol)进行交换反应，TLC跟踪反应。反应完毕，减压旋干反应溶液，再经柱层析提纯，高产率的得到2-N’单三氟甲磺酰胺基-1,3,5三嗪5.41g，产率为95%，纯度为99.9%。
实施例5
在惰性气体保护下，反应温度为60℃，以3-胺基哒嗪(2.50g,26.25mmol)为原料，在100mL乙腈中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(8.95g,25.00mmol)进行交换反应，TLC跟踪反应。反应完毕，减压旋干反应溶液，再经柱层析提纯，高产率的得到3-N’单三氟甲磺酰胺基哒嗪5.11，产率为90%，纯度为99.9%。
实施例6
在惰性气体保护下，反应温度为60℃，以2-胺基吡嗪(2.50g,26.25mmol)为原料，在100mL乙腈中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(8.95g,25.00mmol)进行交换反应，TLC跟踪反应。反应完毕，减压旋干反应溶液，再经柱层析提纯，高产率的得到2-N’单三氟甲磺酰胺基吡嗪5.28g，产率为93%，纯度为99.9%。
实施例7
在惰性气体保护下，反应温度为60℃，以1-氨基异喹啉(3.78g,26.25mmol)为原料，在100mL乙腈中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(8.95g,25.00mmol)进行交换反应，TLC跟踪反应。反应完毕，减压旋干反应溶液，再经柱层析提纯，高产率的得到1-N’单三氟甲磺酰胺基异喹啉6.21g，产率为90%，纯度为99.9%。
实施例8
在惰性气体保护下，反应温度为60℃，以6-溴-1-氨基异喹啉 (5.85g,26.25mmol)为原料，在250mL乙腈中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(8.95g,25.00mmol)进行交换反应，TLC跟踪反应。反应完毕，减压旋干反应溶液，再经柱层析提纯，高产率的得到6-溴-1-N’单三氟甲磺酰胺基异喹啉7.99g，产率为90%，纯度为99.9%。
实施例9
在惰性气体保护下，反应温度为60℃，以8-氨基-1,7-萘(3.81g,26.25mmol)为原料，在250mL乙腈中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶(8.95g,25.00mmol)进行交换反应，TLC跟踪反应。反应完毕，减压旋干反应溶液，再经柱层析提纯，高产率的得到8-N’单三氟甲磺酰胺基-1,7-萘6.37g，产率为92%，纯度为99.9%。
本发明N'-三氟甲磺酰基N杂芳香胺类化合物及其制备方法，在惰性气体保护下，以N杂芳香基氨为原料，在无水非质子溶剂中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶进行反应，高产率得到N'-三氟甲磺酰基N杂芳香胺类化合物，本发明所提供的技术工艺简单，底物选择广泛，后处理纯化方式简便有效，可高效、高产率、高纯度的得到N'-三氟甲磺酰基N杂芳香胺类化合物。
尽管已经示出和描述了本发明的实施例，对于本领域的普通技术人员而言，可以理解在不脱离本发明的原理和精神的情况下可以对这些实施例进行多种变化、修改、替换和变型，本发明的范围由所附权利要求及其等同物限定。

Claims (8)

1.一种N'-三氟甲磺酰基N杂芳香胺类化合物，其特征在于，N'-三氟甲磺酰基N杂芳香胺类化合物具有式的结构式如下：
Figure RE-FDA0002588713630000011
2.如权利要求1所述的N'-三氟甲磺酰基N杂芳香胺类化合物，其特征在于，式中n＝0时，其中X1-X6各自独立地选自碳原子或氮原子且X1-X6至少有一个为氮原子；R1为N杂芳香环上碳原子上所连N'-三氟甲磺酰基
Figure RE-FDA0002588713630000012
Rx为N杂芳香环上所连单个或多个Cl、Br、I、F、三氟甲基、C2-C8氟氢碳链、烷氧基、C1-C18直链或支链烷基。
3.如权利要求1所述的N'-三氟甲磺酰基N杂芳香胺类化合物，其特征在于，式中X1-X6所组成的N杂芳香基团为：吡啶，嘧啶，哒嗪，吡嗪，1,3,5-三嗪中的一种，但不只限于以上N杂芳香基团。
4.如权利要求1所述的N'-三氟甲磺酰基N杂芳香胺类化合物，其特征在于，式中n＝1,2,3,4时，其特征在于，Xn基团分别为三元，四元，五元，六元环，R’x为Xn环上所连单个或多个Cl、Br、I、F、三氟甲基、C2-C8氟氢碳链、烷氧基、C1-C18直链或支链烷基。
5.如权利要求1所述的N'-三氟甲磺酰基N杂芳香胺类化合物，其特征在于，Xn基团为全碳或N杂三元，四元，五元，六元环。
6.一种如权利要求1所述的N'-三氟甲磺酰基N杂芳香胺类化合物的制备方法，其特征在于，包括以下步骤：
在惰性气体保护下，反应温度为30-100℃，以N杂芳香基氨为原料，在无水非质子溶剂中，与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶进行反应，高产率得到N'-三氟甲磺酰基N杂芳香胺类化合物。
7.如权利要求6所述的N'-三氟甲磺酰基N杂芳香胺类化合物的制备方法，其特征在于，N杂芳香基氨与2-[N,N-双(三氟甲烷烷磺酰)氨基]吡啶的摩尔比为1-1.2:1。
8.如权利要求6所述的N'-三氟甲磺酰基N杂芳香胺类化合物的制备方法，其特征在于，所用非质子溶剂包括酮类、醚类、苯类、腈类、卤代烷类、酯类和碳酸酯类，其中酮类选自丙酮、丁酮、甲基乙基酮、甲基叔丁基酮或甲基吡咯烷酮中的一种或多种的组合；醚类选自乙醚、叔丁基甲醚、丙醚、丁醚、异丁醚、四氢呋喃、二氧六环或乙二醇二甲醚中的一种或多种的组合；苯类选自苯、甲苯、二甲苯或三甲苯中的一种或多种的组合；腈类选自乙腈、丙腈、异丙腈中的一种或多种的组合；卤代烷类选自二氯甲烷、氯仿、四氯化碳中的一种或多种的组合；酯类选自乙酸乙酯、乙酸丙酯、乙酸异丙酯、乙酸丁酯或乙酸异丁酯中的一种或多种的组合；碳酸酯类选自碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、碳酸乙烯酯或碳酸丙烯酯中的一种或多种的组合；但不仅限于上述的溶剂。
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