CN102993074A - Synthesis process for 1-o-tolyl-2-thiourea as intermediate of tricyclazole - Google Patents
Synthesis process for 1-o-tolyl-2-thiourea as intermediate of tricyclazole Download PDFInfo
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- CN102993074A CN102993074A CN2012104985130A CN201210498513A CN102993074A CN 102993074 A CN102993074 A CN 102993074A CN 2012104985130 A CN2012104985130 A CN 2012104985130A CN 201210498513 A CN201210498513 A CN 201210498513A CN 102993074 A CN102993074 A CN 102993074A
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- tricyclazole
- phenyl
- methyl
- ethanol
- thiocarbamide
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Abstract
The invention relates to a synthesis process for 1-o-tolyl-2-thiourea as an intermediate of tricyclazole, which is implemented in an environment in which ethanol is used as a solvent. The ethanol is used as an organic solvent, ammonium thiocyanate can be dissolved in the ethanol to generate a byproduct, namely ammonium sulfate which is not dissolved in the ethanol, and therefore, the byproduct can be removed through filtering and other methods; and in addition, the ethanol can be used as the solvent instead of water, so that the generated three wastes are reduced, and the synthesis yield can also be increased.
Description
Technical field
The present invention relates to synthetic method efficient, low toxicity sterilant tricyclazole, disclose the new synthesis process that replaces water method synthesizing tricyclic azoles intermediate o-methyl-phenyl-thiocarbamide take o-toluidine as raw material with solvent method.
Background technology
Tricyclazole is a kind of protective fungicide with strong interior absorption.Can be absorbed by each position of paddy rice rapidly, the lasting period is long, efficacy stability, the low and anti-rain drop erosion of consumption.
Can prevent and treat rice blast.The tricyclazole intermediate o-methyl-phenyl-thiocarbamide of report generally adopts the water method synthetic at present, main technique makes rhodan ammonium soluble in water, then synthesize the o-methyl-phenyl-thiocarbamide with the o-toluidine reaction under certain condition, synthesis yield is about 86%, content about 95%.
In above-mentioned reaction process, because generation by product ammonium sulfate etc. are soluble in water, directly discharging can cause the pollution to environment, as processes and then can greatly improve production cost, and economy is not good, and synthesis yield awaits further raising.
Summary of the invention
The present invention is directed to defects, purpose is to provide a kind of new synthesis process that replaces water method synthesizing tricyclic azoles intermediate o-methyl-phenyl-thiocarbamide take ethanol as solvent.
The technical solution used in the present invention is for this reason: the present invention carries out in the environment take ethanol as solvent.
The present invention is dissolved in rhodan ammonium in the etoh solvent, then o-toluidine and rhodan ammonium alcohol mixeding liquid are pressed the continuous dropwise reaction of speed of 100:85-95 (weight ratio), 70-80 ℃ of control temperature of reaction, reaction solution obtains tricyclazole intermediate o-methyl-phenyl-thiocarbamide by precipitation, washing, press filtration behind the ammonium sulfate that desalination plant generates except dereaction.
Advantage of the present invention is: the present invention is with the ethanol organic solvent, and rhodan ammonium can be dissolved in the ethanol, is insoluble to ethanol and generate by product ammonium sulfate, so can remove by product by methods such as filtrations, it is solvent that ethanol can replace water, reduces the generation of the three wastes, also can improve synthesis yield.
The present invention compares this technique and has reduced the waste water generation with traditional technology, technical process has been simplified in three step unification aftertreatments, can guarantee that synthesis yield 86% brings up to 95%, and product purity brings up to 99% from 95%.
Embodiment
Example 1: with o-toluidine and rhodan ammonium alcohol mixeding liquid adopt respectively charge pump in the tubular reactor by weight (100:95) continuously feeding, about 75 ℃ of control temperature of reaction.Then reaction solution is through the rhodan ammonium of desalination plant except the dereaction generation, then the three steps unification pressure filter that is integrated through precipitation, washing, press filtration, obtain tricyclazole intermediate o-methyl-phenyl-thiocarbamide, synthesis yield reaches 95%(with o-toluidine), content reaches 99%.
Example 2: with o-toluidine and rhodan ammonium alcohol mixeding liquid adopt respectively charge pump in the tubular reactor by weight (100:85) continuously feeding, about 75 ℃ of control temperature of reaction.Then reaction solution is through the rhodan ammonium of desalination plant except the dereaction generation, then the three steps unification pressure filter that is integrated through precipitation, washing, press filtration, obtain tricyclazole intermediate o-methyl-phenyl-thiocarbamide, synthesis yield reaches 92%(with o-toluidine), content reaches 99%.
Example 3: example 2: with o-toluidine and rhodan ammonium alcohol mixeding liquid adopt respectively charge pump in the tubular reactor by weight (100:85) continuously feeding, about 70 ℃ of control temperature of reaction.Then reaction solution is through the rhodan ammonium of desalination plant except the dereaction generation, then the three steps unification pressure filter that is integrated through precipitation, washing, press filtration, obtain tricyclazole intermediate o-methyl-phenyl-thiocarbamide, synthesis yield reaches 90%(with o-toluidine), content reaches 98%.
Claims (2)
1. tricyclazole intermediate o-methyl-phenyl-thiocarbamide synthesis technique is characterized in that, carries out in the environment take ethanol as solvent.
2. tricyclazole intermediate o-methyl-phenyl-thiocarbamide synthesis technique according to claim 1, it is characterized in that, rhodan ammonium is dissolved in the etoh solvent, then o-toluidine and rhodan ammonium alcohol mixeding liquid are pressed continuously dropwise reaction of 100:85-95 (weight ratio), 70-80 ℃ of control temperature of reaction, reaction solution obtains tricyclazole intermediate o-methyl-phenyl-thiocarbamide by precipitation, washing, press filtration behind the ammonium sulfate that desalination plant generates except dereaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104985130A CN102993074A (en) | 2012-11-29 | 2012-11-29 | Synthesis process for 1-o-tolyl-2-thiourea as intermediate of tricyclazole |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012104985130A CN102993074A (en) | 2012-11-29 | 2012-11-29 | Synthesis process for 1-o-tolyl-2-thiourea as intermediate of tricyclazole |
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| CN102993074A true CN102993074A (en) | 2013-03-27 |
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| CN2012104985130A Pending CN102993074A (en) | 2012-11-29 | 2012-11-29 | Synthesis process for 1-o-tolyl-2-thiourea as intermediate of tricyclazole |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112321474A (en) * | 2020-12-16 | 2021-02-05 | 江苏长青农化股份有限公司 | Synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4917255B1 (en) * | 1968-02-28 | 1974-04-27 | ||
| US4234513A (en) * | 1978-05-10 | 1980-11-18 | Hoechst Aktiengesellschaft | Process for the preparation of monoaryl thioureas |
| US4367345A (en) * | 1980-05-06 | 1983-01-04 | Ihara Chemical Industry Co., Ltd. | Process for producing tolylthiourea having high purity |
| US4414211A (en) * | 1978-09-18 | 1983-11-08 | Mcneilab, Inc. | Heterocyclic derivatives of guanidine |
-
2012
- 2012-11-29 CN CN2012104985130A patent/CN102993074A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4917255B1 (en) * | 1968-02-28 | 1974-04-27 | ||
| US4234513A (en) * | 1978-05-10 | 1980-11-18 | Hoechst Aktiengesellschaft | Process for the preparation of monoaryl thioureas |
| US4414211A (en) * | 1978-09-18 | 1983-11-08 | Mcneilab, Inc. | Heterocyclic derivatives of guanidine |
| US4367345A (en) * | 1980-05-06 | 1983-01-04 | Ihara Chemical Industry Co., Ltd. | Process for producing tolylthiourea having high purity |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112321474A (en) * | 2020-12-16 | 2021-02-05 | 江苏长青农化股份有限公司 | Synthesis process of tricyclazole intermediate o-methyl phenylthiosemicarbazide |
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Application publication date: 20130327 |