CN1385423A - N-(4,6-disubstituted 6 pyrimidine-2-)aniline and intermediate products preparation pocess thereof - Google Patents
N-(4,6-disubstituted 6 pyrimidine-2-)aniline and intermediate products preparation pocess thereof Download PDFInfo
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- CN1385423A CN1385423A CN 01118008 CN01118008A CN1385423A CN 1385423 A CN1385423 A CN 1385423A CN 01118008 CN01118008 CN 01118008 CN 01118008 A CN01118008 A CN 01118008A CN 1385423 A CN1385423 A CN 1385423A
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- aniline
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Abstract
The present invention relates to a N(4,6-disubstituted pyrimidine-2-group) aniline and its intermediate product preparation method. Said invention provides its structure formula.
Description
The present invention relates to the preparation method of N-(4, the 6-disubstituted pyrimidines-2-yl) aniline of formula I.
Compound I is a kind of efficient germicide, and it can suppress the pathogenic bacteria protein secreting, comprises reducing some lytic enzyme levels.It all has excellent activity to sensitivity or resistance cause of disease.Thereby Compound I can be used for preventing and treating gray mold, scab of apple of crops such as grape, strawberry, tomato, onion, Kidney bean, cucumber, eggplant and ornamental plant etc.
The use of Compound I report in the literature starts from 1992, but can find out that from CAS accession number [53112-28-0] there is not patent problem in this kind.
Three kinds of reactions describing in " world's agricultural chemicals information manual "/P82 of Liu Changling volume/Chemical Industry Press are:
(1) is starting raw material with urea, methyl ethyl diketone, promptly gets the purpose product through two-step reaction.
(2) with the thiocarbamide be starting raw material, through methylate, oxidation, replacement, hydrolysis make the purpose product.
(3) with the thiocarbamide be starting raw material, through methylate, replacement, cyclization make the purpose product.
The invention provides a kind of new synthetic method.Present method is the compound of first synthesis type II, and then synthetic purpose product.
Present method processing step is short, and the reaction times is few, the reaction conditions gentleness, and the yield height, by product is few.By following specific embodiment method of the present invention is described.
Embodiment 1:N-(4,6-dimethyl pyrimidine-2-yl) aniline adds 50g (0.6mol) ethene acetone with sulfuric acid guanidines 30g, in 60 ℃ the reaction 10 hours after, the decompression precipitation adds the 100ml ethylene dichloride, after the dissolving, pour in the 50ml30%NaOH solution, obtain the 35-40g product, content 95%, yield 96.3%.
Embodiment 2:
Throw 18.6g aniline in the 250ml Erlenmeyer flask, add the 16g vitriol oil, stir, behind the dropping 18.5g cyanamide 0.5h, temperature is reduced to 5 ℃, and filtration drying gets the 26.5-30g product.
Claims (4)
1. the purpose of this invention is to provide the more reasonably preparation method of the guanidines of N-(4, the 6-disubstituted pyrimidines-2-yl) aniline of synthesis type I and/or intermediate product formula II of a kind of reaction scheme and/or reaction conditions.
R wherein
1=C
1-C
6Alkyl, R
2=C
1-C
6Alkyl, C
3-C
6Cycloalkyl, L is ionic group and/or molecular radical, as Phenylsulfonic acid, H
2CO
3, HCI, H
2SO
4, H
3PO
4And salt.
2. according to the preparation method of claim 1, Compound I can obtain by the whole bag of tricks, and its preparation method that we found can obtain by making the reaction of formula II and formula III especially by the following method.
R wherein
1=C
1-C
6Alkyl, R
2=C
1-C
6Alkyl, C
3-C
6Cycloalkyl, R
3=C
1-C
6Alkyl, R
4=C
1-C
6Alkyl, C
3-C
6Cycloalkyl, L is ionic group and/or molecular radical, as Phenylsulfonic acid, H
2CO
3, HCI, H
2SO
4, H
3PO
4
3. according to claim 1,2 preparation method, its temperature of reaction are 30 ℃-150 ℃, and optimal reaction temperature is 50 ℃-100 ℃.
4. according to claim 1,2,3 preparation method, the preparation method of the guanidines of formula II can obtain in the following manner.
According to the preparation method of claim 4, wherein R
5Be mineral acid and/or inorganic salt and/or organic acid and/or cyanamide and/or acid amides and/or prussiate.
According to the preparation method of claim 4, the L of its Chinese style II is ionic group and/or molecular radical, as Phenylsulfonic acid, H
2CO
3, HCI, H
2SO
4, H
3PO
4And salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01118008 CN1385423A (en) | 2001-05-15 | 2001-05-15 | N-(4,6-disubstituted 6 pyrimidine-2-)aniline and intermediate products preparation pocess thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01118008 CN1385423A (en) | 2001-05-15 | 2001-05-15 | N-(4,6-disubstituted 6 pyrimidine-2-)aniline and intermediate products preparation pocess thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1385423A true CN1385423A (en) | 2002-12-18 |
Family
ID=4662916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01118008 Pending CN1385423A (en) | 2001-05-15 | 2001-05-15 | N-(4,6-disubstituted 6 pyrimidine-2-)aniline and intermediate products preparation pocess thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1385423A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106699608A (en) * | 2016-12-26 | 2017-05-24 | 常州大学 | Benzene guanidine containing strong electron withdrawing group and preparation method of salt thereof |
-
2001
- 2001-05-15 CN CN 01118008 patent/CN1385423A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106699608A (en) * | 2016-12-26 | 2017-05-24 | 常州大学 | Benzene guanidine containing strong electron withdrawing group and preparation method of salt thereof |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |