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Reagent and method for detecting nerve agent and analogues thereof

A kit and solvent technology, applied in the field of nerve agents

Inactive Publication Date: 2015-11-04
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far there is no method reported to simultaneously detect sarin, methylphosphine difluoro(2), SOCl 2 , C 2 o 2 Cl 2 , Methylphosphine dichloride (3), 6 and 7

Method used

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  • Reagent and method for detecting nerve agent and analogues thereof
  • Reagent and method for detecting nerve agent and analogues thereof
  • Reagent and method for detecting nerve agent and analogues thereof

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preparation example Construction

[0108] The preparation of the compound of formula I of the present invention can be as shown in the following scheme 1, comprising reacting the compound of the following formula III and formula IV in the presence of a base, thereby obtaining the compound of formula I,

[0109] Process 1

[0110]

[0111] In formula III, IV and I, Z is halogen, R 1 -R 9 as defined above.

[0112] Suitable bases for the above method include, but are not limited to, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, triethylamine, diethylisopropylamine.

[0113] The reaction can also be carried out in a reaction solvent. Suitable reaction solvents include, but are not limited to, high boiling point, aprotic solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetonitrile (CH 3 CN), 1,4-dioxane, etc.

[0114] The reaction can be carried out under heating. For example, the reaction temperature is usually 100-160°C, such as 130-150°C. The reactio...

Embodiment 1

[0138]

[0139] Synthesis of 4-(diethylamino)-2-(3-(diethylamino)phenoxy)benzaldehyde (NA570).

[0140] Compound 9 (1g, 6.05mmol), compound 10 (1g, 3.9mmol) and Na 2 CO 3 (620 mg, 6.05 mmol) in 40 mL of DMF was heated to 140 °C while stirring was continued for 6 hours. The mixture was then cooled to room temperature and the solids were filtered off. Removal of DMF under reduced pressure gave a viscous residue which was purified by flash chromatography using a mixture of petroleum ether and EtOAc (20:1, v / v) as NA570 (1.04 g, colorless solid) , the yield was 78%.

[0141] 1 H NMR (400MHz, CDCl 3 ):δ10.15(s,1H),7.80(d,J=8.0Hz,1H),7.13(t,J=8.0Hz,1H),6.44(d,J=8.0Hz1H),6.42(d,J =8.0Hz,1H),6.40(d,1H),6.25(dd,J=8.0Hz1H),6.07(d,J=2.4Hz,1H),3.32(m,8H),1.14(m,12H);

[0142] 13 C NMR (100MHz, CDCl 3 ): δ187.0, 162.2, 158.3, 153.6, 149.5, 130.2, 129.9, 115.9, 107.3, 106.8, 105.2, 102.499.9, 44.8, 44.4, 12.6, 12.5;

[0143] EI-HRMS(m / z):[M+H] + C 21 h 28 N 2 o 2 , the cal...

Embodiment 2

[0146]

[0147] Compound NA590 was prepared according to the method of Example 1, except that 3-hydroxydoloidine was used instead of 3-diethylaminophenol. NA590's 1 H NMR, 13 C NMR and HRMS data are shown below:

[0148] 1 H NMR (400MHz, CDCl 3 ): δ9.89(s,1H),7.46(s,1H),7.04(t,J=8.0Hz,1H),6.33(d,J=8.0Hz1H),6.32(d,J=4.0Hz,1H ), 5.97(dd, J=8Hz, 1H), 3.32(m, 6H), 3.26(t, J=8Hz, 2H), 2.78(t, J=8Hz, 2H), 2.59(t, J=8Hz, 2H), 1.99(m, 2H), 1.89(m, 2H), 1.16(t, J=8Hz, 6H);

[0149] 13 C NMR (100MHz, CDCl 3 ): δ187.71, 160.60, 154.60, 149.42, 149.10, 130.04, 126.12, 117.94, 117.35, 112.81, 105.68, 101.49, 98.89, 50.05, 49.68, 44.41, 25.39, 11.39, 20.21

[0150] HRMS[M+H] + :365.2232.

[0151] NA590's 1 H NMR and 13 C NMR spectrum as attached Figure 8-9 shown.

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Abstract

The invention relates to a reagent and a method for detecting a nerve agent and analogues thereof, and in particular relates to compounds of formulae I and II in the specification, a detection composition or polymer film containing the compounds, a detection kit containing the composition or polymer film, a preparation method of the compounds and a method for detecting sarin and dangerous substances related with sarin, wherein the definitions of the groups in the formulae I and II are as described in the specification.

Description

technical field [0001] The invention relates to a detection reagent and a detection method for nerve agents, especially sarin and its analogues. Background technique [0002] Sarin is a weapon of mass destruction. It can be absorbed by the human body through the skin or the respiratory tract, further inhibiting acetylcholinesterase, causing paralysis of the nervous system and causing harm to the victim (Somani, S.M. Chemical Warfare Agents: Academic Press, San Diego, 1992). Constrained by the International Chemical Weapons Convention, the possibility of sarin being used for large-scale military use is relatively low. Since its invention in World War II, it has only been used in military affairs during the Iran-Iraq War. But the threat of sarin being used in terrorist attacks against civilians is very real and serious. In the two years between 1994 and 1995, sarin was used in three terrorist attacks, resulting in civilian casualties. According to reports, sarin has also be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C223/06C07C221/00C07D455/04C08L25/06C08K5/18C08K5/3437G01N21/78G01N21/33G01N21/64
Inventor 杨有军雷祖海
Owner EAST CHINA UNIV OF SCI & TECH
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