Unlock instant, AI-driven research and patent intelligence for your innovation.

1-aryl-5-aminotetrazole compound and preparation method thereof

A technology of aminotetrazole and nitrogen-based tetrazole, which is applied in the direction of organic chemistry, can solve the problems of no reaction selectivity, poor atom economy, troublesome raw material synthesis, etc., and achieve easy operation, convenient post-processing, and stability good sex effect

Active Publication Date: 2015-09-02
SHANGHAI UNIV
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The disadvantage is that the reaction will have two tetrazole products with different structures, and there is no good reaction selectivity
[0018] Summarizing the common synthetic methods so far, it is not difficult to see that in the previous synthetic methods, some conditions were relatively harsh, such as high temperature and high pressure, and some raw materials were more troublesome to synthesize, and the atom economy was not good, and most of the methods used Sodium azide, although it is non-flammable, it is explosive, and the conditions and operations need to be strictly controlled when taking it

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 1-aryl-5-aminotetrazole compound and preparation method thereof
  • 1-aryl-5-aminotetrazole compound and preparation method thereof
  • 1-aryl-5-aminotetrazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In a 50 ml reaction bottle, add in sequence, 665 mg (5 mmol) 4-methoxybenzene isonitrile, 3.61 g (12.5 mmol) hypervalent iodine azide reagent, 181 mg (1 mmol) anhydrous copper acetate , 325 mg (1 mmol) of cesium carbonate, then added 30 ml of anhydrous DMF under nitrogen protection, and stirred at 25°C for 12 hours. After the reaction was finished, the solvent was removed and purified by column chromatography to obtain 542 mg of light yellow solid product with a yield of 50%, and the molecular formula was:

[0035]

[0036] H NMR (500 MHz, CDCl 3 ) chemical shift (unit ppm) 7.51 (d, J = 9.0 Hz, 2H), 7.01 (d, J = 9.0 Hz, 2H), 3.85 (s, 3H).

[0037] C NMR spectrum (125 MHz, CDCl 3 ) chemical shift (unit ppm) 160.5, 151.4 , 125.5, 124.3 , 114.7 , 55.6 .

[0038] Infrared Spectrum (KBr): n max 3061, 2945, 2843, 2161, 1597, 1523, 1458, 1255, 1193, 1016, 832,784 cm -1

[0039] Melting point: 84-86 o c.

[0040] In the 50 milliliter reaction bottle, add succe...

Embodiment 2

[0046] In a 50 ml reaction bottle, add successively, 900 mg (5 mmol) 4-bromophenylisonitrile, 3.61 g (12.5 mmol) hypervalent iodine azide reagent, 181 mg (1 mmol) anhydrous copper acetate, 325 mg (1 mmol) of cesium carbonate, then added 30 ml of anhydrous DMF under nitrogen protection, and stirred at 25°C for 12 hours. After the reaction, the solvent was removed,

[0047] Separation and purification by column chromatography gave 731.5 mg of a light yellow solid product with a yield of 55%, and the molecular formula was:

[0048]

[0049] H NMR spectrum (500 MHz, CDCl 3 ) chemical shift (unit ppm) 7.67 (d, J = 8.8Hz, 2H), 7.57 (d, J = 8.8 Hz, 2H).

[0050] C NMR spectrum (125 MHz, CDCl 3 ) chemical shift (in ppm) 151.4, 132.9, 131.8, 123.7, 123.7

[0051] Infrared spectrum (KBr): n max 3053, 2923, 2856, 2148, 1596, 1524, 1458, 1321, 1102, 824 cm -1

[0052] Melting point: 110-113 o c.

[0053] In the 50 milliliter reaction bottle, add successively, 726 milligr...

Embodiment 3

[0060] In a 50 ml reaction bottle, add 655 mg (5 mmol) of 2,4-dimethylbenzeneisonitrile, 3.61 g (12.5 mmol) of hypervalent iodine azide reagent, and 181 mg (1 mmol) of anhydrous Copper acetate, 325 mg (1 mmol) cesium carbonate, and then 30 ml of anhydrous DMF were added under nitrogen protection, and stirred at 25°C for 12 hours. After the reaction was finished, the solvent was removed and purified by column chromatography to obtain 645 mg of light yellow solid product with a yield of 60%, and the molecular formula was:

[0061]

[0062] H NMR spectrum (500 MHz, CDCl 3 ) chemical shift (in ppm) 7.18 (s, 1H), 7.14 (d, J = 7.7 Hz, 1H), 7.10 (d, J = 8.0 Hz, 1H), 2.39 (s, 3H), 2.09 (s, 3H).

[0063] C NMR spectrum (125 MHz, CDCl 3 ) chemical shifts (in ppm) 152.9, 141.6, 134.5 , 132.1 , 128.5 , 127.7 , 126.4 , 21.2 , 17.3 .

[0064] Infrared Spectrum (KBr): n max 3065, 2966, 2923, 2854, 2151, 1612, 1523, 1497, 1457, 1254, 1091, 1018, 864, 805 cm -1

[0065] Melting...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to a 1-aryl-5-aminotetrazole compound and a preparation method thereof. The compound has a structural formula shown in the specification. The method provided by the invention has the characteristics that the raw materials are easy to obtain, the reaction is mild, the operation is simple and convenient and the like, so that the method is suitable for aromatic isocyanides poor or rich in electron. The product obtained by the method provided by the invention belongs to one of tetrazole family, contains relatively more nitrogen atoms, and probably has important applications in the fields of coordination chemistry, biological chemistry, organic chemistry, medicines and the like.

Description

Technical field [0001] The present invention involves a new type of 1-aromatin-5-amino tetrazodizomazole and its preparation methods. technical background [0002] Tetazole refers to a compound containing four nitrogen atoms and a penta nitrogen heteroid structure. The molecular formula is CHN 4 , It has a plane ring skeleton structure and has aroma.Several more common tetzodazole compounds are shown below.Tetrazole is high in nitrogen content, and the molecular structure contains N-N, C-N, N = N, C = N key. It has a high generating 焓 and generates heat to 235.7 kj / mol. It is an important structure of high-energy nitrogen-containing materialsunit.The nitrogen atoms in the molecule have a single electronic or dual -electron orbit, and this five -dollar nitrogen rings have a large π bond structure similar to a benzene ring, so tetrazole molecules are blunt and have high thermal stability. [0003] [0004] (A) (b) (c) [0005] (A) Tetrazole structure (B) 5-amino-1-hydrogen nitrog...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/06
CPCC07D257/06
Inventor 郝健程袁来万文胡青阳蒋海珍
Owner SHANGHAI UNIV