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A kind of preparation method of 2-arylaminoacetamide compounds

A technology for arylaminoacetamides and compounds, which is applied in the field of synthesis of organic compounds, can solve problems such as unfavorable industrial production, and achieve the effects of improving safety and simplifying reaction steps

Active Publication Date: 2017-08-01
凯曦(武汉)生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The existing synthesis methods of 2-arylaminoacetamides need to be carried out in two or more steps, and hazardous chemicals such as boric acid and titanium tetrachloride are used as catalysts in the process, which is not conducive to industrial production

Method used

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  • A kind of preparation method of 2-arylaminoacetamide compounds
  • A kind of preparation method of 2-arylaminoacetamide compounds
  • A kind of preparation method of 2-arylaminoacetamide compounds

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preparation example Construction

[0012] The invention provides a method for preparing 2-arylaminoacetamide compounds. The structural formula of the 2-arylaminoacetamide compounds is as formula (I).

[0013]

[0014] where R 1 is chlorine or hydrogen, R 2 is chlorine, hydrogen, methoxy or tert-butyl, R 3 is cyclohexyl, tert-butyl or n-butyl, R 4 Is methyl, ethyl or 4-chlorophenyl.

[0015] The preparation of 2-arylaminoacetamide compounds is obtained by reacting compound II, compound III and compound IV under the action of a certain amount of compound V, and the specific reaction formula is:

[0016]

[0017] R in compound Ⅱ, Ⅲ and Ⅳ 1 , R 2 , R 3 and R 4 With R in 2-arylaminoacetamide compounds 1 , R 2 , R 3 and R 4 Same definition; Compound V is chloroacetate, wherein R 5 For pyridine, triphenylphosphine or 4-dimethylaminopyridine. In the above reaction, the molar ratio of compounds II, III, IV, and V is 1.2:1:0.8:0.5~0.5:0.8:1:1.5, and the reaction process is as follows: first compound II...

Embodiment 1

[0019] At room temperature, mix 0.106g (1mmol) of benzaldehyde with 0.135g (1mmol) of o-aminoacetophenone, add 2ml of anhydrous methanol, stir and react for 5 minutes, then add 0.109g (1mmol) of Cyclohexylisonitrile and 0.178g (0.5mmol) of triphenylphosphine chloroacetate, the reaction mixture was stirred for 8 hours, after the reaction was completed, it was poured into water, the solid was filtered off, and recrystallized with methanol / water to obtain 0.315g white Crystals are: Yield: 90%, melting point: 188-189°C. The test results are as follows:

[0020]

[0021] IR (cm -1 ) 3332, 3308, 3065, 2936, 2852, 1648, 1602, 1566, 1540, 1513, 1452, 1238, 956, 769.

[0022] 1 H NMR (600MHz, CDCl 3 )δ (ppm): 9.43 (d, J = 3.0Hz, 1H, Ar-NH), 7.82 (d, J = 7.8Hz, 1H, Ar-H), 7.48-7.32 (m, 6H, Ar-H) ,6.76(t,J=7.8Hz,1H,Ar-H),6.67(d,J=8.4Hz,1H,Ar-H),6.43(d,J=7.8Hz,1H,CONH),4.86(d ,J=3.6Hz,1H,COCH),3.82-3.75(m,1H,NCH),2.60(s,3H,CH 3 ),1.86-0.96(m,10H,5CH 2 ).

[0023] 13 C NMR (...

Embodiment 2

[0026] At room temperature, mix 0.163g (1.2mmol) of 4-methoxybenzaldehyde with 0.135g (1mmol) of o-aminoacetophenone, add 2ml of absolute ethanol, stir and react for 2 minutes, then add 0.083g (1mmol) of n-butyl isonitrile and 0.214g (0.6mmol) of triphenylphosphine chloroacetate, the reaction mixture was stirred for 10 hours, after the reaction was completed, it was poured into water, and the solid was filtered out and weighed with methanol / water. Crystallized to obtain 0.319g of white crystals as Yield 90%, melting point: 155°C. The test results are as follows:

[0027]

[0028] IR (cm -1 ) 3331, 3302, 3060, 2929, 2851, 1646, 1600, 1563, 1542, 1511, 1459.

[0029] 1 H NMR (600MHz, CDCl 3 )δ (ppm): 9.42 (s, 1H, Ar-NH), 7.80 (t, J = 7.2Hz, 1H, Ar-H), 7.40-7.37 (m, 3H, Ar-H), 6.91-6.64 ( m,5H,4Ar-H+CONH),4.84(d,J=8.4Hz,1H,COCH),3.79(d,J=6.6Hz,3H,OCH 3 ),3.26-3.22(m,2H,NCH 2 ), 2.58-2.55 (t, J=7.8Hz, 3H, COCH 3 ),1.40-1.38(m,2H,CH 2 ),1.22-1.18(m,2H,CH 2 ),0.84-0.8...

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Abstract

The invention relates to a preparing method of a 2-aroylamino acetamide compound. The general molecular formula of the 2-aroylamino acetamide compound is shown in the specification, the 2-aroylamino acetamide compound is prepared from a compound II, a compound III and a compound IV in a reaction mode under the effect of a compound V, and the preparation reaction formula is shown in the specification, wherein R1 is chlorine or hydrogen, R2 is chlorine or hydrogen or methoxyl or tertiary butyl, R3 is cyclohexyl, tertiary butyl or normal butyl, R4 is methyl or ethyl or 4-chlorphenyl, and the compound V is chloroacetic acid salt. The 2-aroylamino acetamide compound is synthesized in a one-step mode with a one-pot method, and reaction steps are simplified; meanwhile, the chloroacetic acid salt serves as a catalyst, dangerous chemicals such as boric acid and titanium tetrachloride are avoided, and reacting safety is improved.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for preparing 2-arylaminoacetamide compounds. Background technique [0002] 2-Aminoacetamide compounds (see the following formula I for specific structure) have a wide range of pharmacological activities, such as the derivative lidocaine is a local anesthetic for clinical reference, lidocaine also has an antiarrhythmic effect, and has the effect on ventricular Arrhythmia curative effect is good, and the action time is short, no accumulation, no inhibition of myocardial contractility, is the first choice for the treatment of arrhythmia drugs. In addition, 2-arylaminoacetamide compounds have become research hotspots in recent years because of their wide range of pharmacological activities. For example, NPPG has an inhibitory effect on corticotropin releasing factor and has been used in the research of drugs for nervous system diseases. Recent studies have als...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/06C07C237/20
CPCC07C231/06C07C237/20
Inventor 和平吴丽惠
Owner 凯曦(武汉)生物科技有限公司