CN104557751A - 一种用硫脲合成均三嗪胺类物质的方法 - Google Patents
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title claims abstract description 40
- -1 s-triazine amine Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000000126 substance Substances 0.000 title claims abstract description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title abstract 4
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 235000015320 potassium carbonate Nutrition 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract description 5
- 231100000045 chemical toxicity Toxicity 0.000 abstract description 3
- 150000003935 benzaldehydes Chemical class 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 238000000926 separation method Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical class ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical class FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical class ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- IDDAQARKHUGOPH-UHFFFAOYSA-N benzene oxalonitrile Chemical class C1=CC=CC=C1.N#CC#N IDDAQARKHUGOPH-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical class COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
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Abstract
本发明公开了一种用硫脲合成均三嗪胺类物质的方法。所述方法以硫脲和苯甲醛类化合物作为原料,在碱性条件下发生反应,经萃取分离后得到均三嗪胺类化合物。与现有技术相比,本发明的显著优点有:(1)硫脲和甲醛类物质作为原料,与常规的原料相比,价格低廉,来源广泛,化学毒性低,降低合成成本。(2)本反应涉及固液和固固反应,不涉及气相条件,反应设备要求简单。(3)合成条件简单,后处理容易。(4)本反应只需要一步就可以得到目标产物,合成路线简单。
Description
技术领域
本发明属于有机合成领域,具体涉及到含有氨基的均三嗪胺类物质的合成方法。
背景技术
三嗪胺类物质具有广阔的应用领域,是重要的有机中间体,在心血管药物、农药、涂料和染料中占有重要的地位。传统的合成方法有:苯氰类和双氰胺为原料,在乙二醇甲醚作溶剂下,以氢氧化钾作为碱下回流得到目标产物(Yasuda, Takayasu and Nagura, U. S. Pat. Appl. Publ., 20110073007);有报道用苯甲醛和双氰胺为原料,在单质碘崔化学,氨气保护下,在四氢呋喃作为溶剂反应得到目标产物(Shie, Jiun-Jie and Fang, Jim-Min, Journal of Organic Chemisty, 72(8), 3141, 2007 );以高纯度的双氰胺和苯甲氰为原料,以氢氧化钠作为碱在叔丁醇为溶剂下高温反应得到目标产物(雍武刚,马翠萍等,申请号:200610028362.7)有以双氰胺和乙腈为原料,以过量的乙腈和液氨作为溶剂,在碱金属催化下,在高压高温下反应得到目标产物(李健,刘朝慧等,申请号:201210212428.3)。在这些已经报道的方法中,要么合成的原料价格昂贵并且化学毒性较大,要么需要很多步反应才得到目标产物,要么需要在高温高压,并且有气体参与的条件下才能进行反应。
发明内容
本发明的目的在于合成一系列均三嗪胺类化合物,利用硫脲和苯甲醛类物质作为原料,在碱性条件下,得到对应的均三嗪胺类化合物。
实现本发明目的的技术解决方案为:一种用硫脲合成均三嗪胺类物质的方法,以硫脲和苯甲醛类化合物作为原料,在碱性条件下发生反应,经萃取分离后得到均三嗪胺类化合物,所述的苯甲醛类化合物结构表达式如下:
其中,R=H、3-CH3、4-CH3、4-OCH3、3-Cl、3-F、4-Cl或4-CH3CO。
进一步,碱性条件中的碱选自氢氧化钾、碳酸钾或叔丁醇钾等,其用量为苯甲醛类化合物的1-3当量。
进一步,反应温度为80~120℃,反应时间为8~24h。
进一步,反应的溶剂为甲醇、N、N-二甲基甲酰胺、四氢呋喃或二氯甲烷等。
进一步,硫脲用量为苯甲醛类化合物的2~5当量。
本发明与现有技术相比,其显著优点是:
1. 在整个反应中,不需要加入气体,不需要过渡金属作为催化剂,只需要在碱性条件下即可,降低设备的要求和合成的成本;
2. 本反应只需要一步反应即可得到目标产物;
3. 反应结束后,只需要萃取即可得到产物,后处理简单;
4. 合成原料价格低廉,并且化学毒性低,为工业化生产提供了可能。
具体实施方式
本发明的合成路线如下:
R=H、3-CH3、4-CH3、4-OCH3、3-Cl、3-F、4-Cl、4-CH3CO。
具体步骤为:
取0.5mmol的1,2.0mmol的2,碱在耐压管中,加入2ml的有机溶剂,在80-120oC的油浴中,反应8-24h后停止反应,蒸干除去反应溶剂,加入酸性的食盐水洗涤至中性,乙醚萃取,取上层有机相得到目标产物。
实施例1
取两个耐压管,编号为1,2号,在三个耐压管中加入0.5mmol(68.5mg),2.0mmol(152.0mg)的硫脲,0.5mmol (60.0mg)的对甲基苯甲醛在耐压管中,其中1号加入276mg的碳酸钾,2号加入三乙胺206mg,在120oC下加入乙醇,反应24h,反应结束后旋干溶剂,用酸洗使pH为7,用乙酸乙酯萃取取上层液,经过柱层析得到的目标产物的产物分别为:79%,58%。
实施例2
取三个耐压管,编号为1,2,3号,在三个耐压管中加入0.5mmol(68.5mg),2.0mmol(152.0mg)的硫脲,0.5mmol (60.0mg)的对甲基苯甲醛在耐压管中,其中1号加入69mg的碳酸钾,2号加入138mg的碳酸钾,3号加入276mg的碳酸钾,在120oC下加入乙醇,反应24h,反应结束后旋干溶剂,用酸洗使pH为7,用乙酸乙酯萃取取上层液,经过柱层析得到的目标产物的产物分别为:45%,55%,79%。
实施例3
取六个耐压管,编号为1,2,3,4号,在4个耐压管中加入0.5mmol(68.5mg),2.0mmol(152.0mg)的硫脲,0.5mmol (60.0mg) 的对甲基苯甲醛, 276mg的碳酸钾在耐压管中,其中1号加入甲醇,2号加入N,N-二甲基甲酰胺,3号加入四氢呋喃,4号加入二氯甲烷,在120oC下反应24h,反应结束后旋干溶剂,用酸洗使pH为7,用乙酸乙酯萃取取上层液,经过柱层析得到的目标产物的产物分别为: 79%,45%,46%,45%。
实施例4
取八个耐压管,编号为1,2,3,4,5,6,7,8号,在八个耐压管中加入0.5mmol(68.5mg),2.0mmol(152.0mg)的硫脲, 276mg的碳酸钾在耐压管中,加入2ml的甲醇,其中1号加入0.5mmol (53.0mg)的苯甲醛,2号加入0.5mmol (60.0mg)的3-甲基苯甲醛,3号加入0.5mmol(60.0mg)的4-甲基苯甲醛,4号加入0.5mmol(68.0mg)的4-甲氧基苯甲醛,5号加入0.5mmol(70.0mg)的3-氯苯甲醛,6号加入0.5mmol(62.0mg)的3-氟苯甲醛,7号加入0.5mmol(70.0mg)的4-氯苯甲醛,8号加入0.5mmol (74.0mg)4-乙酰苯甲醛,八个反应在120oC下反应24h,反应结束后旋干溶剂,用酸洗使pH为7,用乙酸乙酯萃取取上层液,经过柱层析得到的目标产物的产物分别为:90%, 93%, 94%, 95%, 85%, 83%, 89%, 85%。
Claims (5)
1.一种用硫脲合成均三嗪胺类物质的方法,其特征在于,以硫脲和苯甲醛类化合物作为原料,在碱性条件下发生反应,经萃取分离后得到均三嗪胺类化合物,所述的苯甲醛类化合物结构表达式如下:
其中,R=H、3-CH3、4-CH3、4-OCH3、3-Cl、3-F、4-Cl或4-CH3CO。
2.如权利要求1所述的用硫脲合成均三嗪胺类物质的方法,其特征在于,碱性条件中的碱选自氢氧化钾、碳酸钾或叔丁醇钾中任意一种,其用量为苯甲醛类化合物的1-3当量。
3.如权利要求1所述的用硫脲合成均三嗪胺类物质的方法,其特征在于,反应温度为80~120℃,反应时间为8~24h。
4.如权利要求1所述的用硫脲合成均三嗪胺类物质的方法,其特征在于,反应的溶剂为甲醇、N、N-二甲基甲酰胺、四氢呋喃或二氯甲烷中任意一种。
5.如权利要求1所述的用硫脲合成均三嗪胺类物质的方法,其特征在于,硫脲用量为苯甲醛类化合物的2~5当量。
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CN113058651A (zh) * | 2019-12-31 | 2021-07-02 | 南京理工大学 | 基于蜜勒胺衍生物的二维配位聚合物电催化剂的制备方法 |
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CN113058651B (zh) * | 2019-12-31 | 2023-05-05 | 南京理工大学 | 基于蜜勒胺衍生物的二维配位聚合物电催化剂的制备方法 |
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