CN1235886C - Method for preparing sulfhydyl-(m-benzamido) phenyl tetrazole - Google Patents
Method for preparing sulfhydyl-(m-benzamido) phenyl tetrazole Download PDFInfo
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- CN1235886C CN1235886C CN 200410014471 CN200410014471A CN1235886C CN 1235886 C CN1235886 C CN 1235886C CN 200410014471 CN200410014471 CN 200410014471 CN 200410014471 A CN200410014471 A CN 200410014471A CN 1235886 C CN1235886 C CN 1235886C
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- benzoyl
- phenyl tetrazole
- benzoylamino
- sulfydryl
- generate
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Abstract
The present invention discloses a method for producing 5-mercapto-1-(m-benzamido) phenyl tetrazole, which comprises the steps: m-nitro aniline and benzoyl chloride are reacted to generate m-trobenzanilide under the existence of benzene, the m-trobenzanilide is reacted to generate m-aminobenzanilide under the existence of hydrazine hydrate and catalyst iron trichloride, the m-aminobenzanilide, acetonitrile, triethylamine, CS2 and ethyl chloroformate are mixed and react to generate m-n-butyl isothiocyanate benzanilide ester, and the m-n-butyl isothiocyanate benzanilide ester and sodium azide react to generate the 5-mercapto-1-(m-benzamido) phenyl tetrazole under the existence of dimethylformamide. The present invention has the advantages of simple technology, easy operation and high product yield, and the product yield reaches more than 80%.
Description
Technical field:
The present invention relates to a kind of production method of nitrogen-containing heterocycle compound.
Background technology:
The production method complexity of 5-sulfydryl-1-in the prior art (benzoylamino) phenyl tetrazole, yield is low.
Summary of the invention:
The object of the present invention is to provide a kind of technology simple, the production method of 5-sulfydryl-1-that the product yield is high (benzoylamino) phenyl tetrazole.
Technical solution of the present invention is:
The production method of a kind of 5-sulfydryl-1-(benzoylamino) phenyl tetrazole, its feature: comprise the following steps: successively
1. with m-nitraniline and Benzoyl chloride in the presence of benzene, reaction generates N-benzoyl-m-nitraniline;
2. with N-benzoyl-m-nitraniline in the presence of hydrazine hydrate, catalyzer iron trichloride, reaction generates N-benzoyl-m-aminophenyl amine;
3. with N-benzoyl-m-aminophenyl amine and acetonitrile, triethylamine, dithiocarbonic anhydride, Vinyl chloroformate hybrid reaction, generate a N-benzoyl-isothiocyanic acid diboronic ester;
4. with a N-benzoyl-isothiocyanic acid diboronic ester and sodiumazide in the presence of dimethyl formamide, reaction generates 5-sulfydryl-1-(benzoylamino) phenyl tetrazole
1. step reacts under reflux state.2. step reacts under reflux state.Step temperature of reaction 4. is 60～100 ℃.
Technology of the present invention is simple, and is easy to operate, and product yield height reaches more than 80%.
The invention will be further described below in conjunction with embodiment:
Embodiment:
Embodiment:
1. m-nitraniline is mixed with benzene, Benzoyl chloride; under reflux state, react 2～10 hours (example 2,4,6,8,10 hours); the consumption of above-mentioned substance (mol ratio) is: m-nitraniline: benzene: Benzoyl chloride=1: 10～30: 0.6～1.8 (example 1: 10: 1.2,1: 20: 0.6,1: 30: 1.8); after cooling, transfer PH to 8～10 then with 10% liquid caustic soda; after normal pressure boils off benzene; solid is separated out in cooling, and suction filtration is washed neutrality and promptly obtained N-benzoyl-m-nitraniline.
2. with N-benzoyl-m-nitraniline; solvent---methyl alcohol; iron trichloride; hydrazine hydrate mixes; 4～48 hours (examples 4 of back flow reaction; 15; 30; 48 hours); the amount ratio of above-mentioned substance (mol ratio) is: N-benzoyl-m-nitraniline: methyl alcohol: hydrazine hydrate=1: 20～60: 2～10 (example 1: 60: 5; 1: 40: 10; 1: 20: 2); the consumption of iron trichloride is 0.1～10% (example 0.1% of m-nitro formylaniline by weight; 1%; 5%; 10%); reaction finishes after-filtration; filtrate boils off 3/4ths solvent; solid is separated out in cooling; suction filtration is washed neutrality and is promptly obtained N-benzoyl-m-aminophenyl amine.
3. with N-benzoyl-m-aminophenyl amine and acetonitrile; triethylamine; dithiocarbonic anhydride; Vinyl chloroformate mixes; 4～20 hours (examples 2 of stirring reaction under the room temperature; 10; 20 hours); the amount ratio of above-mentioned substance (mol ratio) is N-benzoyl-m-aminophenyl amine: acetonitrile: triethylamine: dithiocarbonic anhydride: Vinyl chloroformate=1: 10～30: 0.5～8: 0.8～2.5: 0.8～2.5 (can be 1: 10: 4: 1.8: 2.5; 1: 20: 8: 2.5: 0.8; 1: 30: 0.5: 0.8: 1.8); solid, suction filtration are again separated out in cooling; washing; acetonitrile is washed; wash neutrality dry a N-benzoyl-isothiocyanic acid diboronic ester.
4. with water; sodiumazide is stirred to dissolving; be warmed up to 50～100 ℃ of (examples 50; 80; 100 ℃); drip DMF (dimethyl formamide) solution of a N-benzoyl-isothiocyanic acid diboronic ester; 60～100 ℃ of (examples 60; 80; 100 ℃) 2～12 hours (examples 2 of insulation; 6; 10; 12 hours) reaction; the amount ratio of above-mentioned substance (mol ratio) is a sodiumazide: water: isothiocyanic acid benzanilide ester a: DMF=1: 30～150: 1: 0.5～2 (examples 1: 30: 1: 1.2; 1: 90: 1: 0.5; 1: 150: 1: 2); add the vitriol oil after reaction finishes and transfer PH to 2; separate out solid; suction filtration, wash product 5-sulfydryl-1-(benzoylamino) phenyl tetrazole.
Claims (4)
1, the production method of a kind of 5-sulfydryl-1-(benzoylamino) phenyl tetrazole is characterized in that: comprise the following steps: successively
1. with m-nitraniline and Benzoyl chloride in the presence of benzene, reaction generates N-benzoyl-m-nitraniline;
2. with N-benzoyl-m-nitraniline in the presence of hydrazine hydrate, catalyzer iron trichloride, reaction generates N-benzoyl-m-aminophenyl amine;
3. with N-benzoyl-m-aminophenyl amine and acetonitrile, triethylamine, dithiocarbonic anhydride, Vinyl chloroformate hybrid reaction, generate a N-benzoyl-isothiocyanic acid diboronic ester;
4. with a N-benzoyl-isothiocyanic acid diboronic ester and sodiumazide in the presence of dimethyl formamide, reaction generates 5-sulfydryl-1-(benzoylamino) phenyl tetrazole
2, the production method of 5-sulfydryl-1-according to claim 1 (benzoylamino) phenyl tetrazole, it is characterized in that: 1. step reacts under reflux state.
3, the production method of 5-sulfydryl-1-according to claim 1 and 2 (benzoylamino) phenyl tetrazole, it is characterized in that: 2. step reacts under reflux state.
4, the production method of 5-sulfydryl-1-according to claim 1 and 2 (benzoylamino) phenyl tetrazole, it is characterized in that: step temperature of reaction 4. is 60～100 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410014471 CN1235886C (en) | 2004-03-24 | 2004-03-24 | Method for preparing sulfhydyl-(m-benzamido) phenyl tetrazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410014471 CN1235886C (en) | 2004-03-24 | 2004-03-24 | Method for preparing sulfhydyl-(m-benzamido) phenyl tetrazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1562983A CN1562983A (en) | 2005-01-12 |
| CN1235886C true CN1235886C (en) | 2006-01-11 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 200410014471 Expired - Fee Related CN1235886C (en) | 2004-03-24 | 2004-03-24 | Method for preparing sulfhydyl-(m-benzamido) phenyl tetrazole |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102906075B (en) * | 2010-03-12 | 2016-01-13 | 拜耳知识产权有限责任公司 | The preparation method of the 1-alkyl tetrazolium that 5-replaces |
| CN104098522A (en) * | 2014-07-25 | 2014-10-15 | 南通市华峰化工有限责任公司 | Preparation method for 5-sulfydryl-1-phenyl tetrazole |
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Granted publication date: 20060111 Termination date: 20140324 |