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Method for synthesizing N,N'-dialkylurea

A dialkyl urea compound technology, applied in the field of organic synthetic chemistry, can solve the problems of low atom economy, high toxicity of isocyanate, damage to the environment and equipment, etc., and achieve the effect of broad development prospects

Inactive Publication Date: 2015-04-29
NANJING UNIV OF SCI & TECH
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  • Abstract
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  • Claims
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Problems solved by technology

One of the traditional methods of synthesizing N,N'-dialkylurea is generated by the reaction of isocyanate and primary amine. Although it is widely used, the raw material isocyanate used in this method is highly toxic and seriously pollutes the environment. The other It is obtained through the coupling reaction of phenylurea derivatives and halogenated hydrocarbons under the catalytic conditions of palladium and other catalysts. Although this method has a wide range of applications, the atom economy of this method is low, and the by-products generated by the reaction Hydrohalic acid has a certain destructive effect on the environment and equipment, and cannot meet the requirements of green chemistry.

Method used

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  • Method for synthesizing N,N'-dialkylurea
  • Method for synthesizing N,N'-dialkylurea
  • Method for synthesizing N,N'-dialkylurea

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: 1,3-benzhydryl urea

[0020] 1,3-dibenzylurea

[0021]

[0022] Urea (60.06mg, 1mmol), [Cp*IrCl 2 ] 2 (3.2mg, 0.04mmol, 0.4mol%) and sodium hydroxide (40mg, 1mmol), benzyl alcohol (108.14mg, 1mmol) and 1ml tert-amyl alcohol were sequentially added to a 10ml microwave reaction flask. After the reaction mixture was reacted at 110°C for 3 hours, it was cooled to room temperature, the solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether), yield: 85% 1 H NMR (500MHz, CDCl 3 )δ7.30-7.28(m,4H,ArH),7.26-7.23(m,6H,ArH),4.89(t,J=5.0Hz,2H,AlkylNH),4.33(d,J=5.7Hz,4H, 2xCH 2 ); 13 C NMR (125MHz, CDCl 3 )δ158.4, 139.2, 128.5, 127.3, 127.2, 44.4.

Embodiment 2

[0023] Example 2: 1,3-bis(4-methoxy)benzylurea

[0024] 1,3-bis(4-methoxybenzyl)urea

[0025]

[0026] Urea (60.06mg, 1mmol), [Cp*IrCl 2 ] 2 (3.2mg, 0.04mmol, 0.4mol%) and sodium hydroxide (40mg, 1mmol), p-methoxybenzyl alcohol (138.16mg, 1mmol) and 1ml tert-amyl alcohol were added to a 10ml microwave reaction flask in turn. After the reaction mixture was reacted at 110°C for 3 hours, it was cooled to room temperature, the solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether), yield: 86%

[0027] 1,3-bis(4-methoxybenzyl)urea(5ka).mp176-177℃; 1 H NMR (500MHz,DMSO)δ7.17(s,4H,ArH),6.87(s,4H,ArH),6.29(s,2H,AlkylNH),4.14(s,4H,CH 2 ),3.72(s,6H,OCH 3 ); 13 C NMR (125MHz, DMSO) δ158.0, 157.9, 132.7, 128.3, 113.6, 55.0, 42.4.

Embodiment 3

[0028] Example 3: 1,3-bis(4-trifluoromethyl)benzylurea

[0029] 1,3-bis(4-(trifluoromethyl)benzyl)urea

[0030]

[0031] Urea (60.06mg, 1mmol), [Cp*IrCl 2 ] 2 (3.2mg, 0.04mmol, 0.4mol%) and sodium hydroxide (40mg, 1mmol), p-trifluorobenzyl alcohol (176.14mg, 1mmol) and 1ml tert-amyl alcohol were sequentially added to a 10ml microwave reaction flask. After the reaction mixture was reacted at 110°C for 3 hours, it was cooled to room temperature, the solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether), yield: 75%

[0032] mp170-171℃; 1 H NMR (500MHz, DMSO-d 6 )δ7.68(d,J=7.3Hz,4H,ArH),7.46(d,J=7.2Hz,4H,ArH),6.68(t,J=5.4Hz,2H,AlkylNH),4.31(d,J =4.8Hz,4H,CH 2 ); 13 CNMR (125MHz, DMSO-d 6 )δ158.0, 145.9, 127.5, 127.2 (q, J C-F =31.6Hz),125.0(d,J C-F =3.5Hz),124.3(q,J C-F =270Hz), 42.6.

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Abstract

The invention discloses a method for synthesizing N,N'-dialkylurea. The method comprises the following steps: adding urea, benzyl alcohol, a transition metal catalyst iridium complex, alkali and tert-amyl alcohol in a reaction container, performing reaction on a reaction mixture in a microwave reactor for several hours at 100-130 DEG C, and then cooling to room temperature. Compared with the prior art, the method disclosed by the invention is started from the raw material, namely urea, which is simple and easy to obtain, N,N'-dialkylurea is obtained by performing coupling reaction with alcohol which is more environment-friendly; furthermore, a generated byproduct is water, so that the reaction is in line with the requirements of green chemistry and has broad development prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing N,N'-dialkylurea. Background technique [0002] N,N'-dialkylurea is a very important class of nitrogen-containing compounds, which widely exist in natural products and drug structures, and have a wide range of pharmacological and physiological activities, for example, some of them act as transient voltage receptor cation channels ( TRPV1) antagonist (A-42561), urotensin II receptor antagonist (ACT-058362), α7 nicotinic acetylcholine receptor agonist (α7nAChR), mitogen-activated kinase (MAP) inhibitor, etc. One of the traditional methods of synthesizing N,N'-dialkylurea is generated by the reaction of isocyanate and primary amine. Although it is widely used, the raw material isocyanate used in this method is highly toxic and seriously pollutes the environment. The other It is obtained through the coupling reaction of pheny...

Claims

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Application Information

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IPC IPC(8): C07C275/24C07C273/18
Inventor 孙春楼渠攀攀李峰
Owner NANJING UNIV OF SCI & TECH
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