CN102993176A - Novel synthetic process of nicosulfuron - Google Patents
Novel synthetic process of nicosulfuron Download PDFInfo
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- CN102993176A CN102993176A CN201210430437XA CN201210430437A CN102993176A CN 102993176 A CN102993176 A CN 102993176A CN 201210430437X A CN201210430437X A CN 201210430437XA CN 201210430437 A CN201210430437 A CN 201210430437A CN 102993176 A CN102993176 A CN 102993176A
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- nicosulfuron
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Abstract
The invention provides a novel synthetic process of nicosulfuron. According to the novel synthetic process of nicosulfuron, based on an one-pot reaction, N, N-dimethyl-2-aminosulfonyl-picolinamide, 2-amino-4, 6-dirnethoxypyrimidine, acid-binding agent and solvent are fed into a reaction kettle at one time; and methylclhlorofonmate and catalyst are sequentially dropwise added at temperature below room temperature, and finally heating reflux reaction is carried out. By adopting the novel synthetic process of nicosulfuron, the total recovery of the nicosulfuron is over 88%.
Description
Technical field
The invention belongs to technical field of pesticide, relate in particular to a kind of new synthetic process background technology of nicosulfuron
Nicosulfuron is a kind of acetolactate synthestase (ALS) inhibitor, is a kind of efficient, low toxicity, dedicated herbicide for novel corn field that Environmental compatibility is good.The synthetic method of nicosulfuron mainly is N at present; the intermediate that N-dimethyl-2-amido alkylsulfonyl-picolinamide and Vinyl chloroformate reaction generate; again with 2-amino-4; 6-dimethoxypyridin condensation reaction (removing by product ethanol by rectifying tower in the reaction process) generates the former medicine of nicosulfuron.This technique needs two-step reaction, and intermediate needs just can enter next step condensation reaction after the drying, and simultaneously final step condensation reaction need to be used rectifying tower, so this technique, long reaction time, and labour intensity is larger, the waste energy.
Summary of the invention
Purpose of the present invention is to provide a kind of new synthetic process of nicosulfuron, and novel process adopts one kettle way, simplifies reaction unit, and Reaction time shorten reduces energy expenditure, and the product total recovery reaches more than 88%.
Its technical scheme is: adopt methyl-chloroformate to replace Vinyl chloroformate, adopt organic bases as acid binding agent, adopt ethylene dichloride or methylene dichloride or acetonitrile as solvent.First with N, N-dimethyl-2-amido alkylsulfonyl-picolinamide, 2-amino-4,6-dimethoxy pyrimidine, acid binding agent and solvent once drop in the reactor, then are sequentially added into methyl-chloroformate and catalyzer under the room temperature being lower than, and add rear temperature rising reflux reaction.
Its technique effect is: adopt the method for the treatment of different things alike, without rectifying tower, simplified reaction unit, shortened the reaction times, reduce labour intensity, reduce the waste of energy.
Embodiment
In 500 milliliters of four-hole boiling flasks of thermometer, agitator and prolong are housed; the N that adds 0.05 mole; N-dimethyl-2-amido alkylsulfonyl-picolinamide, 0.05 mole 2-amino-4; 6-dimethoxypyridin and triethylamine; the methylene dichloride that adds 200 milliliters; open and stir; be cooled to about 20 ℃; begin to be sequentially added into 0.06 mole methyl-chloroformate and an amount of catalyzer, finish, the temperature rising reflux reaction; reaction finishes through aftertreatment; get nicosulfuron 18.1 grams, with N, N-dimethyl-2-amido alkylsulfonyl-picolinamide calculated yield 88.3%.
Claims (3)
1. the new synthetic process of a nicosulfuron; it is characterized in that: this process using one kettle way; with N; N-dimethyl-2-amido alkylsulfonyl-picolinamide, 2-amino-4; 6-dimethoxypyridin, acid binding agent and solvent once drop in the reactor; then be sequentially added into methyl-chloroformate and catalyzer under the room temperature being lower than, add rear temperature rising reflux reaction.
2. the new synthetic process of nicosulfuron according to claim 1, it is characterized in that: the acid binding agent of this process using is organic bases, optimum is triethylamine.
3. the new synthetic process of nicosulfuron according to claim 1, it is characterized in that: the solvent of this process using is ethylene dichloride or methylene dichloride or acetonitrile, optimum is methylene dichloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210430437XA CN102993176A (en) | 2012-11-02 | 2012-11-02 | Novel synthetic process of nicosulfuron |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210430437XA CN102993176A (en) | 2012-11-02 | 2012-11-02 | Novel synthetic process of nicosulfuron |
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| CN102993176A true CN102993176A (en) | 2013-03-27 |
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| CN201210430437XA Pending CN102993176A (en) | 2012-11-02 | 2012-11-02 | Novel synthetic process of nicosulfuron |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483318A (en) * | 2013-09-25 | 2014-01-01 | 安徽丰乐农化有限责任公司 | Environment-friendly novel technology for synthesizing high content nicosulfuron |
| CN112645930A (en) * | 2020-12-30 | 2021-04-13 | 邯郸市瑞田农药有限公司 | Nicosulfuron water-phase method synthesis process |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87100436A (en) * | 1986-01-30 | 1987-08-12 | 石原产业株式会社 | The pyridinsulfonamide compounds that replaces, the method that contains the weedicide of this compounds and prepare this compounds |
| CN87101735A (en) * | 1986-03-07 | 1987-09-16 | 纳幕尔杜邦公司 | Herbicidal pyridine sulfonamides |
| WO1990005728A1 (en) * | 1988-11-21 | 1990-05-31 | E.I. Du Pont De Nemours And Company | Process for the interconversion of two separate crystal forms of a herbicidal pyridine sulfonamide |
| CN101903379A (en) * | 2007-12-20 | 2010-12-01 | 拜尔农作物科学股份公司 | Herbicidal compound based on N-azine group-N '-pyridyl sulfonylurea |
| CN102007119A (en) * | 2008-04-18 | 2011-04-06 | 石原产业株式会社 | Method for producing pyrimidine compound |
-
2012
- 2012-11-02 CN CN201210430437XA patent/CN102993176A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87100436A (en) * | 1986-01-30 | 1987-08-12 | 石原产业株式会社 | The pyridinsulfonamide compounds that replaces, the method that contains the weedicide of this compounds and prepare this compounds |
| CN87101735A (en) * | 1986-03-07 | 1987-09-16 | 纳幕尔杜邦公司 | Herbicidal pyridine sulfonamides |
| WO1990005728A1 (en) * | 1988-11-21 | 1990-05-31 | E.I. Du Pont De Nemours And Company | Process for the interconversion of two separate crystal forms of a herbicidal pyridine sulfonamide |
| CN101903379A (en) * | 2007-12-20 | 2010-12-01 | 拜尔农作物科学股份公司 | Herbicidal compound based on N-azine group-N '-pyridyl sulfonylurea |
| CN102007119A (en) * | 2008-04-18 | 2011-04-06 | 石原产业株式会社 | Method for producing pyrimidine compound |
Non-Patent Citations (1)
| Title |
|---|
| 李翔等: "烟嘧黄隆的合成", 《现代农药》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483318A (en) * | 2013-09-25 | 2014-01-01 | 安徽丰乐农化有限责任公司 | Environment-friendly novel technology for synthesizing high content nicosulfuron |
| CN112645930A (en) * | 2020-12-30 | 2021-04-13 | 邯郸市瑞田农药有限公司 | Nicosulfuron water-phase method synthesis process |
| CN112645930B (en) * | 2020-12-30 | 2022-08-09 | 邯郸市瑞田农药有限公司 | Nicosulfuron water-phase method synthesis process |
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Application publication date: 20130327 |