CN106699688A - 一种苯基哌嗪硫醚及其制备方法 - Google Patents
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
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Abstract
本发明涉及一种苯基哌嗪硫醚及其制备方法，该化合物为4,6‑二甲基‑1,3‑双‑2,2′‑苯基哌嗪硫醚，以1,3‑二甲基苯为起始原料，通过4步反应合成，苯基哌嗪硫醚化合物是制备聚芳硫醚的中间体,用这种中间体制成的塑料不仅具有优良的热性能和尺寸的热塑性，而且具有稳定性、憎水性、阻燃性和力学性能和高折射率的性能；其制备方法原料便宜易得，合成方法简单，是一种合成哌嗪硫醚化合物的全新方法。
Description
技术领域
本发明涉及化合物生产领域，尤其是一种苯基哌嗪硫醚及其制备方法。
背景技术
苯基哌嗪硫醚化合物是制备聚芳硫醚的中间体,用这种中间体制成的塑料不仅具有优良的热性能和尺寸的热塑性，而且具有稳定性、憎水性、阻燃性和力学性能和高折射率的性能(Synthesis of molecular chains:phenylene thioether and sulfoxideoligomers。Tetrahedron,64(27),6281-6288；2008)。
发明内容
本发明所要解决的技术问题在于提供一种苯基哌嗪硫醚。
本发明所要解决的另一技术问题在于提供上述苯基哌嗪硫醚的制备方法。
为解决上述技术问题，本发明的技术方案是：
一种苯基哌嗪硫醚，4,6-二甲基-1,3-双-2,2′-苯基哌嗪硫醚，其结构式为(Ⅰ)所示，
优选的，上述苯基哌嗪硫醚，4,6-二甲基-1,3-双-2,2′-苯基哌嗪硫醚的核磁共振氢谱数据为2.285(s，6H)，2.831-2.669(d,16H),6.563-6.544(d,2H),6.932-6.897(t,2H),7.135-7.068(q,4H),7.251(s,1H),7.408(s,1H)。
上述苯基哌嗪硫醚的制备方法，以1,3-二甲基苯为起始原料，通过4步反应合成目标化合物，具体步骤如下：
(1)化合物1 1,3-二甲基苯进行碘化得到化合物2；
(2)化合物2通过催化剂与化合物3溴苯硫醇反应得到化合物4；
(3)化合物4与化合物5进行Buchwald反应得到化合物6；
(4)化合物6通过三氟乙酸去保护得到目标化合物7；其中，
上述苯基哌嗪硫醚的制备方法中的中间产物化合物4，其结构式为(Ⅱ)所示，
上述苯基哌嗪硫醚的制备方法中的中间产物化合物6，其结构式为(Ⅲ)所示，
上述苯基哌嗪硫醚的制备方法的具体反应方程式如下：
本发明的有益效果是：
上述哌嗪硫醚4,6-二甲基-1,3-双-2,2′-苯基哌嗪硫醚是制备聚芳硫醚塑料的中间体，用这种中间体制成的塑料不仅具有优良的热性能和尺寸的热塑性，而且具有稳定性、憎水性、阻燃性和力学性能和高折射率的性能；其制备方法原料便宜易得，合成方法简单，是一种合成哌嗪硫醚的全新方法，适合规模化工业生产的需要。
附图说明
图1为4,6-二甲基-1,3-双-2,2′-苯基哌嗪硫醚的HNMR谱图。
具体实施方式
为了使本领域的技术人员更好的理解本发明的技术方案，下面结合具体实施方式对本发明所述技术方案作进一步的详细说明。
实施例1
4,6-二甲基-1,3-双-2,2′-苯基哌嗪硫醚的制备方法，具体步骤如下：
(1)将131g碘溶于100ml冰乙酸和300ml醋酸酐的混合体系中，用吹风机加热至40℃后，分批加入34g三氧化铬，体系温度升至60℃，将体系降温至50℃,缓慢将化合物1滴加到上述体系中，温度控制在40℃，滴加结束后，降温至30℃以下(冰水降温)，开始滴加浓硫酸，滴加结束后温度20℃。15min后，体系升温至60℃，反应1h后，TLC检测(纯PE)，从TLC上看，已反应完全，将体系倒入到1L的冰水中，析出的固体，固体用DCM溶解，水相用500ml DCM萃取，合并有机相，有机相用1L水洗一次，1L饱和食盐水洗一次,干燥，浓缩得一粘油状液体，静置，次日析出晶体，过滤，得到33g白色固体(化合物2)。收率20％。
(2)将物料17.5g化合物2和20.3g化合物3，叔丁醇钾12.1g的三(二亚苄基丙酮)二钯Pd2(dba)3，1.1g，0.5g的双(2-二苯基膦)苯醚(DPEphos)，依次加入到三口反应瓶无水200ml甲苯中，氮气置换5次，升温至100℃，此时体系为灰褐色，反应过夜。TLC(纯PE)(产物Rf＝0.5)反应完全，降温至室温，过滤，滤液用PE和DCM洗涤，滤液中析出大量固体，再过滤，晾干得17.1g白色固体(化合物4)。收率89％。
(3)20℃，依次将物料15g化合物4，17.3g化合物5,9g叔丁醇钠，1.7g的Pd2(dba)3，1.5g的BINAP加入到150ml的甲苯中，氮气置换5次，升温至回流，反应过夜。TLC检测，(PE:EA＝5:1)反应完全，降温，过滤，滤饼用EA洗涤，滤液加水500ml，分液，水相EA萃取(200ml*2)，有机相用饱和食盐水洗一次，干燥，浓缩，经柱层析纯化，浓缩析出白色固体10.3g，母液缩干得4g浅棕色固体(化合物6)。收率66.8％
(4)将4g化合物6溶于400ml的DCM中，缓慢加入2ml的三氟乙酸，20℃反应过夜。TLC(PE:EA＝5:1),反应完全，向体系中加入2M的稀盐酸，析出白色固体，过滤，固体用8％氢氧化钠溶液调PH至9，过滤，固体经甲醇洗涤纯化得1.05g白色固体(目标产物化合物7)。收率37％。经检测，如图1所示，4,6-二甲基-1,3-双-2,2′-苯基哌嗪硫醚的HNMR谱图如下：2.285(s，6H)，2.831-2.669(d,16H),6.563-6.544(d,2H),6.932-6.897(t,2H),7.135-7.068(q,4H),7.251(s,1H),7.408(s,1H)。
上述具体反应方程式如下：
应用试验例
实施例1中目标产物采用常规方法制备聚芳硫醚树脂，经检测玻璃化温度(Tg)高达235-241℃，耐热性能突出；其阻燃等级为UL-94V-0级；其透光率高达85％(450nm)，折射率为1.7-1.74。
上述参照具体实施方式对该一种苯基哌嗪硫醚及其制备方法进行的详细描述，是说明性的而不是限定性的，可按照所限定范围列举出若干个实施例，因此在不脱离本发明总体构思下的变化和修改，应属本发明的保护范围之内。
Claims (5)
1.一种苯基哌嗪硫醚，其特征在于：为4,6-二甲基-1,3-双-2,2′-苯基哌嗪硫醚，其结构式为(Ⅰ)所示，
2.根据权利要求1所述的苯基哌嗪硫醚，其特征在于：4,6-二甲基-1,3-双-2,2′-苯基哌嗪硫醚的核磁共振氢谱数据为2.285(s，6H)，2.831-2.669(d,16H),6.563-6.544(d,2H),6.932-6.897(t,2H),7.135-7.068(q,4H),7.251(s,1H),7.408(s,1H)。
3.权利要求1所述苯基哌嗪硫醚的制备方法，其特征在于：以1,3-二甲基苯为起始原料，通过4步反应合成目标化合物，具体步骤如下：
(1)化合物1 1,3-二甲基苯进行碘化得到化合物2；
(2)化合物2通过催化剂与化合物3溴苯硫醇反应得到化合物4；
(3)化合物4与化合物5进行Buchwald反应得到化合物6；
(4)化合物6通过三氟乙酸去保护得到目标化合物7；其中，
4.权利要求3所述苯基哌嗪硫醚的制备方法中的中间产物化合物4，其特征在于：其结构式为(Ⅱ)所示，
5.权利要求3所述苯基哌嗪硫醚的制备方法中的中间产物化合物6，其特征在于：其结构式为(Ⅲ)所示，
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