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Pyrazole tetrazole carboxamide and synthesis method thereof

A technology of pyrazole tetrazolium amide and phenylpyrazole amide, which is applied in the field of pyrazole tetrazolium amide derivatives and their microwave synthesis, can solve the problems of high energy consumption, long reaction time, and many side reactions. Achieve the effect of short reaction time, high yield and high killing activity

Inactive Publication Date: 2012-03-21
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The traditional synthesis method has high energy consumption, long reaction time and many side reactions

Method used

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  • Pyrazole tetrazole carboxamide and synthesis method thereof
  • Pyrazole tetrazole carboxamide and synthesis method thereof
  • Pyrazole tetrazole carboxamide and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of 3-methyl-1-phenyl-N-(1-hydrogen-tetrazol-5-yl)-1-hydrogen-pyrazole-5-amide

[0025] In a 250ml four-neck flask, add 0.01mol of 3-methyl-1-phenyl-1-hydrogen-pyrazole-5-acyl chloride, 0.01mol of 5-aminotetrazole, dissolve in 100ml of toluene, and irradiate the mixture under 400W microwave Under the light, heat to 110°C, react for 20min, cool and filter. The product was obtained by recrystallization with ethanol, the yield: 85%. Melting point: 223~225℃.

[0026]

[0027] 1 H NMR (DMSO-d6, 300MHz): 2.27(s, 3H, CH 3 ), 6.83(s, 1H, pyrazole C-H), 7.38-7.41(m, 5H, Ar-H), 9.39-9.41(t, 1H, -NH-CO-), 14.26(s, 1H, tetrazole N-H).

[0028] IR (cm -1 ): 3131, 2976, 1701, 1658, 1314.

[0029] The bactericidal activity test shows that: when the concentration is 10ppm, the bactericidal rate of sulfate-reducing bacteria and iron bacteria reaches 90.9% and 76% respectively in 1 hour.

Embodiment 2

[0031] Synthesis of 3-methyl-N-(1-hydro-tetrazol-5-yl)-1-p-tolyl-1-hydro-pyrazole-5-amide.

[0032] In a 250ml four-neck flask, add 0.01mol of 3-methyl-1-p-tolyl-1-hydro-pyrazole-5-acyl chloride), 0.012mol of 5-aminotetrazole, dissolve in 100ml of ethanol, and Under microwave irradiation, heat to 115°C, react for 5 minutes, cool and filter. The product was obtained by recrystallization with toluene, yield: 73%. Melting point: 246-247°C.

[0033]

[0034] 1 H NMR (DMSO-d6, 300MHz): 2.24(s, 3H, CH 3 ), 2.27 (s, 3H, CH 3 ), 6.83 (s, 1H, pyrazole C-H), 7.19-7.36 (m, 4H, Ar-H), 9.41 (d, 1H, -NH-CO-), 14.19 (s, 1H, tetrazole N-H) .

[0035] IR (cm -1 ): 3140, 2972, 1699, 1606, 1377.

[0036] The bactericidal activity test shows that: when the concentration is 10ppm, the bactericidal rate of sulfate-reducing bacteria and iron bacteria reaches 92.2% and 78.3% respectively in 1h.

Embodiment 3

[0038] Synthesis of 1-(4-methoxyphenyl)-3-methyl-N-(1-hydrogen-tetrazol-5-yl)-1-hydrogen-pyrazole-5-amide

[0039] In a 250ml four-neck flask, add 0.01mol of 1-(4-methoxyphenyl)-3-methyl-1-hydrogen-pyrazole-5-acid chloride, 0.015mol of 5-aminotetrazole, dissolve in 100ml of toluene , under 300W microwave irradiation, heated to 110°C, reacted for 15min, cooled and filtered. The product was obtained by recrystallization from ethanol, with a yield of 82%. Melting point: 229-231°C.

[0040]

[0041] 1 H NMR (DMSO-d6, 300MHz): 2.24(s, 3H, CH 3 ), 3.80 (s, 3H, OCH 3 ), 6.83 (s, 1H, pyrazole C-H), 7.10-7.35 (m, 4H, Ar-H), 9.41 (d, 1H, -NH-CO-), 14.26 (s, 1H, tetrazole N-H) .

[0042] IR (cm -1 ): 3134, 2964, 1691, 1602, 1312.

[0043] The bactericidal activity test shows that: when the concentration is 10ppm, the bactericidal rates of sulfate-reducing bacteria and iron bacteria reach 91.3% and 80% respectively in 1 hour.

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Abstract

The invention discloses pyrazole tetrazole carboxamide and a synthesis method thereof. The compound is as shown in a formula, wherein R is hydrogen, C1-C5 are alkyl, and C1-C5 are alkoxy, halogen or nitro. A pyrazole tetrazole carboxamide derivative is synthesized under microwave irradiation with substituted pyrazole acyl chloride and tetrazole amide with an equivalent ratio of 1: (1-1.5), the microwave power is 100-400W, and the reaction time of microwave radiation is 5-20min. The invention has the advantages that: (1) the reaction speed is greatly increased due to adoption of microwave radiation, and the reaction time is 5-20min; and (2) the reaction operation is easy, and the reaction yield is high. The synthesized pyrazole tetrazole carboxamide derivative has high killing activity for iron bacteria and sulfate reducing bacteria.

Description

technical field [0001] The invention relates to a pyrazole tetrazolium amide derivative and a synthesis method thereof, in particular to a pyrazole tetrazolium amide derivative and a microwave synthesis method thereof. Background technique [0002] In recent years, heterocyclic chemistry has been a major component of organic chemistry. In today's organic compounds, the number of heterocyclic compounds accounts for about one-third of the total. Nitrogen-containing heterocyclic compounds are an important branch of heterocyclic compounds. As intermediates of pharmaceuticals, pesticides, dyes and other fine chemical products, nitrogen-containing heterocyclic compounds and their derivatives are more and more widely used. [0003] Pyrazoles are a class of substances with a wide range of biological activities. Pyrazole derivatives play a very important role in pesticides due to their high efficiency, low toxicity and multi-directional substitution on the pyrazole ring. At prese...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A01P1/00
Inventor 徐炎华胡俊周桃玉
Owner NANJING UNIV OF TECH
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