CN116768853A - 一种由吡啶基吡唑醛制备吡啶基吡唑酰氯的方法及其应用 - Google Patents
一种由吡啶基吡唑醛制备吡啶基吡唑酰氯的方法及其应用 Download PDFInfo
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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Abstract
本发明属于有机合成领域,具体涉及一种由吡啶基吡唑醛制备吡啶基吡唑酰氯的方法及其应用,反应式如下:
Description
技术领域
本发明属于有机合成领域,具体涉及一种由吡啶基吡唑醛制备吡啶基吡唑酰氯的方法,及其在制备酰胺类化合物的应用。
背景技术
吡啶基吡唑酰氯一类重要的有机合成中间体,可制备酰胺类化合物。例如,吡啶基吡唑酰氯与苯胺反应,可制备高效、安全的新型酰胺类杀虫剂氯虫苯甲酰胺、溴氰虫酰胺、四唑虫酰胺、环溴虫酰胺、硫虫酰胺、氟氯虫双酰胺或四氯虫酰胺。中国专利ZL200810103211.2公开了“一种制备3-卤代-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰卤的方法”。
本发明所示的由吡唑醛与氯化试剂反应,制备酰氯的方法未见公开。
发明内容
本发明的目的在于提供一种制备吡啶基吡唑酰氯的新方法。
为实现上述目的,本发明采用技术方案为:
一种由吡啶基吡唑醛(I)制备吡啶基吡唑酰氯(II)的方法,反应式如下
式I或II中:
X选自H或Cl;
Y选自溴或
通式(I)所示的吡啶基吡唑醛与氯化试剂反应,制得通式(II)所示的吡啶基吡唑酰氯。
将通式(I)所示的吡啶基吡唑醛与其1~10倍摩尔的氯化试剂,在有或者无催化剂存在下,在溶剂中、-10℃至溶剂沸点范围内进行氯化反应0.5~48小时,制得通式(II)所示的吡啶基吡唑酰氯;所述溶剂的摩尔用量为通式(I)所示的吡啶基吡唑醛的2~500倍。
所述氯化试剂选自磺酰氯、氯气、N-氯代丁二酰亚胺、二氯海因或三氯异氰尿酸,优选磺酰氯;
所述催化剂选自偶氮二异丁腈、偶氮二异庚腈、偶氮二异丁酸二甲酯或过氧化苯甲酰,优选偶氮二异丁腈或过氧化苯甲酰;
所述溶剂选自二氯甲烷、氯仿、四氯化碳、己烷、苯、氯苯、甲苯、乙酸乙酯、乙腈、四氢呋喃、二氧六环或二甲基亚砜,优选氯苯、甲苯、乙腈、二氧六环或己烷。
进一步地,所述通式(I)所示的吡啶基吡唑醛与氯化试剂和催化剂的加料摩尔比为1:1~5:0~0.1,反应温度为50℃到溶剂沸点之间,反应时间1~10小时。
本发明还包括经由上述制备方法得到的吡啶基吡唑酰氯在制备酰胺类化合物的应用。
吡啶基吡唑酰氯(II)与通式(IV)所示的取代苯胺反应,可以制备通式(III)所示的酰胺类化合物,
式II、式III或式IV中,
X选自H或Cl;
Y选自溴或
W选自O或S;
R1选自氯、溴或甲基;
R2选自氯或氰基;
R3选自氢或氟;
R4选自氢、甲基、异丙基或
所述吡啶基吡唑酰氯与取代苯胺反应的过程是将所述通式(II)所示的吡啶基吡唑酰氯与通式(IV)所示的取代苯胺进行缩合反应,制备通式(III)所示的酰胺类化合物。表1列出了部分通式(III)化合物的结构。
表1、部分通式(III)化合物的结构
本发明所具有的优点:
本发明提供了一种新的制备吡唑酰氯的方法。经本发明所述方法制得的吡唑酰氯,可应用于多种具有应用价值的酰胺类化合物的制备。
应明确的是,在本发明的权利要求所限定的范围内,可进行各种变换和改动。
具体实施方式
下列合成实例可用来进一步说明本发明,但不意味着限制本发明。
实施例1
1-(3,5-二氯-2-吡啶基)-3-溴-1-H-吡唑-5-甲酰氯的合成
(1)、1-(3,5-二氯-2-吡啶基)-3-溴-1-H-吡唑-5-甲醛的合成
向反应瓶中依次加入1-(3,5-二氯-2-吡啶基)-3-溴-1-H-吡唑-5-甲醇(37.4克,116毫摩尔,按文献J.Heterocyclic Chem.,23,897(1986)中的方法制得)、200毫升二氯甲烷,室温搅拌下分批加入氯铬酸吡啶盐(50克,232毫摩尔),加毕回流反应4小时。反应结束后经柱色谱提纯得白色固体20克,收率53.8%,HPLC归一含量95%,熔点107-109℃。
1H NMR(600MHz,CDCl3):9.79(s,1H),8.45(d,1H),7.96(d,1H),7.10(s,1H)。
(2)、1-(3,5-二氯-2-吡啶基)-3-溴-1-H-吡唑-5-甲酰氯的合成
向反应瓶中依次加入1-(3,5-二氯-2-吡啶基)-3-溴-1-H-吡唑-5-甲醛(3.46克,10毫摩尔)、50毫升氯苯、偶氮二异丁腈(16毫克,0.1毫摩尔),室温搅拌下缓慢滴加磺酰氯(3.37克,25毫摩尔),加毕80℃反应8小时。减压下蒸干溶剂,得到红色油3.5克,收率99%。
1H NMR(600MHz,CDCl3):8.44(d,1H),7.94(d,1H),7.29(s,1H)。
应用实施例1
3-溴-N-(2,4-二氯-6-(甲氨酰基)苯基)-1-(3,5-二氯-2-吡啶基)-1H-吡唑-5-甲酰胺(杀虫剂四氯虫酰胺)的合成
向反应瓶中,依次加入2-氨基-3-5-二氯苯甲酰甲胺(2.1克,9.5毫摩尔)、20毫升乙腈,将实施例1得到的1-(3,5-二氯-2-吡啶基)-3-溴-1-H-吡唑-5-甲酰氯(3.5g,9.9毫摩尔)溶于20毫升乙腈,缓慢滴入上述反应液中,室温搅拌10分钟后,缓慢加热至回流,加热回流2.5小时。柱色谱提纯得白色固体5克,收率93.5%,HPLC归一含量95.6%,熔点188-190℃。
1H NMR(600MHz,CDCl3):9.98(s,1H),8.39(d,1H),7.84(d,1H),7.31(s,1H),7.19(d,1H),7.11(d,1H),6.47(d,1H),2.86(d,3H)。
按照上述的制备方法还可以制备其它通式(III)所示的酰胺类杀虫化合物。
Claims (9)
1.一种由吡啶基吡唑醛(I)制备吡啶基吡唑酰氯(II)的方法,其特征在于:反应式如下:
式I或II中:
X选自H或Cl;
Y选自溴或
通式(I)所示的吡啶基吡唑醛与氯化试剂反应,制得通式(II)所示的吡啶基吡唑酰氯。
2.按照权利要求1所述的制备方法,其特征在于:将通式(I)所示的吡啶基吡唑醛与其1~10倍摩尔的氯化试剂,在有或者无催化剂存在下,在溶剂中、-10℃至溶剂沸点范围内进行氯化反应0.5~48小时,制得通式(II)所示的吡啶基吡唑酰氯;所述溶剂的摩尔用量为通式(I)所示的吡啶基吡唑醛的2~500倍。
3.按照权利要求2所述的制备方法,其特征在于:所述氯化试剂选自磺酰氯、氯气、N-氯代丁二酰亚胺、二氯海因或三氯异氰尿酸。
4.按照权利要求2所述的制备方法,其特征在于:所述催化剂选自偶氮二异丁腈、偶氮二异庚腈、偶氮二异丁酸二甲酯或过氧化苯甲酰。
5.按照权利要求2所述的制备方法,其特征在于:所述溶剂选自二氯甲烷、氯仿、四氯化碳、己烷、苯、氯苯、甲苯、乙酸乙酯、乙腈、四氢呋喃、二氧六环或二甲基亚砜。
6.按照权利要求3所述的制备方法,其特征在于:所述氯化试剂选自磺酰氯。
7.按照权利要求4所述的制备方法,其特征在于:所述催化剂选自偶氮二异丁腈或过氧化苯甲酰。
8.按照权利要求5所述的制备方法,其特征在于:所述溶剂选自氯苯、甲苯、乙腈、二氧六环或己烷。
9.一种按照权利要求1所述制备方法,得到的吡啶基吡唑酰氯在制备酰胺类化合物(III)中的应用,其特征在于:反应式如下:
式II、式III或式IV中,
X选自H或Cl;
Y选自溴或
W选自O或S;
R1选自氯、溴或甲基;
R2选自氯或氰基;
R3选自氢或氟;
R4选自氢、甲基、异丙基或
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