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Preparation method of N-formamide compound

A technology for formamides and compounds, which is applied in the field of preparation of N-formamides, can solve the problems of troublesome post-processing, complicated operation and high cost, and achieve the effects of convenient post-processing, low risk and less generation of three wastes

Inactive Publication Date: 2013-02-27
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to address the defects of the prior art methods, to provide a preparation method for efficiently converting halogenated compounds into N-formamide compounds, which overcomes the disadvantages of high cost, troublesome post-processing, cumbersome operation, and low yield.

Method used

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  • Preparation method of N-formamide compound
  • Preparation method of N-formamide compound
  • Preparation method of N-formamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: N-benzamide (SL-1)

[0027]

[0028] Add 3.93g (0.025mol) bromobenzene, 85mL (2.5mol) formamide, 0.20g (0.0025mol) copper oxide, 0.42g (0.0025mol) potassium iodide and 3.45g (0.025mol) potassium carbonate in a 250mL three-necked flask. Heat the reaction in an oil bath at 180°C for 3h, and stir mechanically. After the reaction is complete, the reaction liquid is cooled to room temperature, and after adding excess water, it is extracted with dichloromethane. After combining the organic phases, it is extracted once with saturated saline. After the organic layer is dried with anhydrous sodium sulfate and allowed to stand for a while, it is filtered. The filtrate was distilled under reduced pressure to obtain 2.71 g of the product with a yield of 89.5%.

[0029] 1 H-NMR (400MHz, CDCl 3 ):7.08-7.19(m,2H,Ar-H),7.32-7.38(m,2H,Ar-H),7.54(d,J=8.0Hz,1H,Ar-H),8.38(s,1H, CHO).

[0030] 13 C-NMR (100MHz, CDCl 3 ):δ=120.1(2C),125.2,129.7(2C),137.6,159.6.

[00...

Embodiment 5

[0037] Embodiment 5: N-p-methylbenzamide (SL-2)

[0038]

[0039] The reaction steps are the same as in Example 1, except that the raw material is 0.025 mol of p-methylbromobenzene, which is heated and reacted in an oil bath at 120°C for 10 h to obtain 3.08 g of N-p-toluamide, with a yield of 91.2%.

[0040] 1 H-NMR (400MHz, CDCl 3 ):2.21(s,1H,CH 3 ), 7.20(d, J=8.0Hz, 2H, Ar-H), 7.54(d, J=8.0Hz, 2H, Ar-H), 8.70(s, 1H, CHO).

[0041] 13 C-NMR (100MHz, CDCl 3 ):δ=22.3, 120.8(2C), 132.8(2C), 135.4, 137.6, 160.2.

Embodiment 6

[0042] Embodiment 6: N-butyl formamide (SL-3)

[0043]

[0044] Add 3.42g (0.025mol) of 1-bromobutane, 0.96mL (0.025mol) of formamide, 20mL of toluene, 0.42g (0.0025mol) of potassium iodide and 2.5g (0.025mol) of potassium bicarbonate into a 100mL three-necked flask. Heat at 120°C under reflux in an oil bath for 6 hours, and stir mechanically. After the reaction is complete, cool the reaction solution to room temperature, remove part of the solvent by rotary evaporation, add excess water to the residue and extract it with chloroform, combine the organic phases and extract it once with saturated saline, and dry the organic layer with anhydrous sodium sulfate After standing for a period of time, it was filtered, and the filtrate was distilled under reduced pressure to obtain 2.36 g of the product, with a yield of 93.4%.

[0045] 1 H-NMR (400MHz, CDCl 3 ):0.9(t,J=7.7Hz,3H,CH 3 ),1.28-1.36(m,2H,CH 2 ),1.48-1.54(m,2H,CH 2),3.14-1.20(m,2H,CH 2 ), 8.04(s,1H,CHO).

[0046] ...

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Abstract

The invention relates to a preparation method of N-formamide compounds, which comprises the following steps of: using halides and formamide as raw materials, reacting under the heating backflow for 3-10 hours under the conditions of solvent or no solvent, acid-binding agent and catalyst or no catalyst, and after reaction, conducting post-treatment such as extraction to reaction liquid to obtain the N-formamide compounds, wherein the ratio of amount of substance of the halides to amount of substance of the formamide is 1: (1-100) and the reaction is preferably conducted under the condition of no solvent. The preparation method provided by the invention has the advantages of high yield, convenience in post-treatment, low catalyst cost, simpleness in operation, moderate condition, easiness in reaction control, smaller quantity of three kinds of produced wastes (waste gas, waste water and waste residue), small risk and the like, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of N-formamide compounds, belonging to the field of organic synthesis. Background technique [0002] N-formamide compounds are a class of important compounds, such as N-benzamides, which can be used as organic synthesis reagents and amino protection agents, etc., while amides are also important pharmaceutical intermediates, such as N-( 4-(4-(2-methoxyphenyl) piperazine) butyl formamide is an important intermediate in the synthesis of dopamine D3 receptor partial agonist BP897. The application of N-formamide compounds is very extensive and has huge commercial value . [0003] At present, the research on the synthesis of N-formamide compounds has been widely concerned by the majority of chemists, especially researchers in the field of catalytic chemistry. Usually, the synthesis of N-formamide compounds is realized by reacting free primary or secondary amine compounds with formic acid in the presence of a ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/03C07C231/08C07D239/42C07D295/13
Inventor 徐崇福富利祥陆海玲郑黄利宋蕴丽赵萌萌
Owner CHANGZHOU UNIV
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