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Preparation method of formamide derivative

A technology for formamide and derivatives, which is applied in the field of preparation of formamide derivatives, can solve the problems of complex reaction process, high energy consumption, many three wastes and the like, and achieves the effects of convenient post-processing, simple operation and low cost

Inactive Publication Date: 2014-07-02
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are few reports on the addition reaction of formamide and olefins, and there are mainly the following: There are literatures (Tetrahedron Letters, 39(1 / 2): 59-62, 1998) that report that formamide and styrene are added through four-step reaction. Although the yield is better (90%), the reaction process is complicated, and reagents such as relatively expensive mercuric trifluoroacetate and sodium borohydride are used, so it is not suitable for industrial production; there are also documents (Australian Journal of Chemistry, 59( 3): 218-224, 2006) reported that a ruthenium complex was used to catalyze the reaction of formamide and styrene, and 72% of the addition product could be obtained at 180°C for 24 hours, but the reaction energy consumption was too large; another report (Tetrahedron Letters , 49(37): 5380-5382, 2008) added sulfuric acid to the addition reaction of formamide and styrene, and reacted under toluene reflux for 18 hours to obtain a yield of 63%. High, not suitable for mass production applications

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  • Preparation method of formamide derivative

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Effect test

Embodiment 1

[0019] The preparation of embodiment 1, N-ethylformamide

[0020] Add 1mol formamide (45g), 4g methyltriphenylphosphonium iodide and 140mL 1,4-dioxane into the autoclave, replace the air in the autoclave with nitrogen, and then introduce 3mol ethylene (84g), and heat up to The reaction was completed with stirring at 70°C for 5 hours. Pour the obtained reaction solution into cold water (about 100ml), filter, and distill the obtained filtrate under reduced pressure (0.003MPa), collect the fraction at 65~72°C to obtain 68g of N-ethylformamide, with a yield of 93%.

[0021] Change the type and amount of olefin in Example 1 (R1), the amount of 1,4-dioxane added (V1 for short), the amount of methyl triphenylphosphonium iodide added (C1 for short), and the reaction temperature ( Abbreviated as T) and reaction time (referred to as t), the yield of the corresponding formamide derivative is Y. See Table 1 for detailed data.

Embodiment 2~5

[0023] Table 1

[0024] Example

[0025] instruction manual:

Embodiment 2

[0026] Example 2 is to collect fractions at 68-75°C, and the resulting product is N-isopropylformamide.

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Abstract

The invention discloses a preparation method of formamide derivative. The method comprises the steps that formamide and alkene shown in the formula II are reacted in solvent under the catalysis of methyltriphenylphosphonium iodide; the mol ratio of formamide to alkene to methyltriphenylphosphonium iodide is 1:(2-5):(0.05-0.02), the reaction temperature is 60 to 80 DEG C, and the reaction time is 3 to 6 hours; reaction liquid is conducted to reduced pressure distillation after reaction, so as to obtain the formamide derivative shown in the formula I; and in the formula I, R refers to ethyl, isopropyl, phenethyl, tertiary butyl or cyclohexyl. The method has the characteristics of simplicity in operation during the reaction process, convenience in aftertreatment, high yield and the like.

Description

technical field [0001] The invention relates to a preparation method of formamide derivatives. Background technique [0002] Formamide derivatives containing N substituents are chemical intermediates that can be used in the synthesis of various medicines and pesticides, as well as organic solvents and extractants. The use of addition reactions to derive substituents on N is a relatively novel method that has gradually attracted the attention of researchers. At present, there are few reports on the addition reaction of formamide and olefins, and there are mainly the following: There are literatures (Tetrahedron Letters, 39(1 / 2): 59-62, 1998) that report that formamide and styrene are added through four-step reaction. Although the yield is better (90%), the reaction process is complicated, and reagents such as relatively expensive mercuric trifluoroacetate and sodium borohydride are used, so it is not suitable for industrial production; there are also documents (Australian Jo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/03C07C231/08
Inventor 陈新志周少东葛新
Owner ZHEJIANG UNIV