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Synthesis method of substituted urea compound

A synthesis method and compound technology, applied in the field of organic compound synthesis, can solve the problems of low substrate toxicity, danger of phosgene or isocyanate, mild reaction conditions, etc., and achieve the effects of low substrate toxicity, short reaction time, and mild reaction conditions.

Active Publication Date: 2021-03-30
XIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a synthetic method for substituted urea compounds, which solves the problem that phosgene or isocyanate is more dangerous in existing methods, and its substrate toxicity is relatively small, and the reaction conditions are mild

Method used

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  • Synthesis method of substituted urea compound
  • Synthesis method of substituted urea compound
  • Synthesis method of substituted urea compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] Add 0.2mmol (1eq) N-phenylurea, 200μL of dry dichloromethane to the reaction test tube in turn, then add 14.4μL (0.1eq) of HMPA to the test tube, then add 0.2mmol (1eq) of benzaldehyde, After reacting for 10 minutes under ice bath, 1.2 eq of trichlorosilane was added, and the reaction was monitored after reacting for 12 hours.

[0037] After the reaction is complete, quench the unreacted trichlorosilane with water, then add saturated sodium bicarbonate solution to adjust the pH to about 7-8, then transfer the reaction solution into a separatory funnel and extract it with ethyl acetate. Water Na 2 SO 4 Dry and filter. After the solvent was removed under reduced pressure, N-benzyl-N'-phenylurea was obtained as a white solid by column chromatography.

[0038] The NMR data of N-benzyl-N'-phenylurea is characterized by:

[0039] 1 H NMR (400MHz, DMSO–d 6 )δ8.56(s,1H),7.45–7.38(m,2H),7.38–7.29(m,4H),7.24(m,J=8.4,7.2,1.8Hz,3H),6.96–6.84(m, 1H), 6.62 (t, J=6....

Embodiment 2

[0042]

[0043] The same preparation process as in Example 1, the aldehyde used was 4-fluorobenzaldehyde, and the product obtained was N-(4-fluorobenzyl)-N'-phenylurea, which was a white solid.

[0044] NMR data of N-(4-fluorobenzyl)-N'-phenylurea is characterized by:

[0045] 1 H NMR (400MHz, DMSO–d 6 )δ8.57(s,1H),7.41(dd,J=8.6,1.0Hz,2H),7.38–7.32(m,2H),7.27–7.11(m,4H),6.90(t,J=7.3Hz , 1H), 6.63 (t, J=6.0Hz, 1H), 4.28 (d, J=5.9Hz, 2H).

[0046] The melting point of N-(4-fluorobenzyl)-N'-phenylurea is: M.p 158.9~160.2°C.

Embodiment 3

[0048]

[0049] The same as the preparation process of Example 1, the aldehyde used was 4-chlorobenzaldehyde, and the product obtained was N-(4-chlorobenzyl)-N'-phenylurea, which was a white solid.

[0050] The NMR data of N-(4-chlorobenzyl)-N'-phenylurea is characterized by:

[0051] 1 H NMR (400MHz, DMSO–d 6 )δ8.60(s,1H),7.41(dd,J=8.6,2.1Hz,4H),7.33(d,J=8.5Hz,2H),7.27–7.19(m,2H),6.90(t,J =7.3Hz, 1H), 6.66(t, J=6.0Hz, 1H), 4.29(d, J=6.0Hz, 2H).

[0052] The melting point of N-(4-chlorobenzyl)-N'-phenylurea is: M.p 139.8~139.9°C.

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Abstract

The invention discloses a synthesis method of a substituted urea compound, which comprises the following steps: stirring aldehyde, N-aryl urea, trichlorosilane and Lewis base in an organic solvent ata temperature range of -20 DEG C to room temperature for reaction, and carrying out after-treatment to obtain the substituted urea compound, wherein the molar ratio of the aldehyde to the N-aryl ureais 1: (1-2), the molar ratio of the aldehyde to the Lewis base is 1:(0.01-5), the molar ratio of the aldehyde to trichlorosilane is 1:(1-2), R1 is a C1-C5 saturated alkyl group, or an unsubstituted orsubstituted aromatic ring, and R2 is H, an electron withdrawing substituent or an electron donating substituent. According to the method, trichlorosilane is catalyzed by small molecular Lewis base, reductive alkylation of urea is realized, synthesis can be realized by a one-pot method, and the method is simple to operate, short in reaction time, low in substrate toxicity, low in cost, easy to obtain, mild in reaction condition and high in safety.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a synthesis method of substituted urea compounds. Background technique [0002] Urea and urea derivatives have important applications in natural organic compounds and medicinal chemistry. Compounds with different uses can be obtained by modifying the nitrogen atoms of urea compounds in molecules. Such compounds are widely used in medicine, pesticides, materials, and combinatorial chemistry. And it has a wide range of applications in catalysts. [0003] At present, the method of preparing urea derivatives is mainly through the preparation of amines and phosgene or commercially available isocyanates. Although these raw materials have the characteristics of toxicity and high risk, they are still widely used in industrialization. [0004] Trichlorosilane is an important organosilicon monomer, mainly used in the synthesis of organosilanes, alkyl groups, aryl grou...

Claims

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Application Information

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IPC IPC(8): C07C273/18C07C275/28C07D333/20C07D307/52C07D307/54C07C311/58C07C303/40
CPCC07C273/1863C07C273/189C07D333/20C07D307/52C07D307/54C07C303/40C07C275/28C07C311/58
Inventor 王周玉冉小云钱珊杨羚羚蒋珍菊李奎吴静胡旭马园
Owner XIHUA UNIV
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