Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of triazolopyrimidine sulfydryl type compound

The technology of an azolopyrimidine thiol compound, which is applied in the field of preparation of triazolopyrimidine thiol compounds, can solve the problem of foul-smelling methyl mercaptan, and achieve the effect of being beneficial to industrial production and solving the problem of methyl mercaptan odor

Active Publication Date: 2014-06-25
ORIENTAL LUZHOU AGROCHEM
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the conversion rate of this method is high, a large amount of methyl mercaptan (Ⅵ) with a foul smell is produced in the reaction, which has serious environmental problems.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of triazolopyrimidine sulfydryl type compound
  • Preparation method of triazolopyrimidine sulfydryl type compound
  • Preparation method of triazolopyrimidine sulfydryl type compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of 5-ethoxy-7-fluoro-[1,2,4]-triazolo-[1,5-C]-pyrimidine-2(3H)thione

[0021] Add 10.0g (0.048mol, purity 96%) 5-methoxy-7-fluoro-[1,2,4]-triazolo-[4,3-C]-pyrimidine-3(2H)thione Into 40g ethanol. At 0°C-10°C, 5.4 g of sodium ethoxide was added to the above solution. The mixture was stirred at 0°C-10°C for 2h. Then the mixture was acidified with 9.5 g of 36% concentrated hydrochloric acid, 50 g of water was added, and the mixture was stirred at -5°C for 30 min, and then filtered. The filter cake was washed with 20 ml of cold water and 20 ml of cold ethanol and dried to obtain 9.2 g of the target compound, which was an off-white solid.

[0022] NMR(CDCl 3 )δ: 1 H: 1.47 (t, 3H), 4.69 (q, 2H), 7.04 (d, 1H).

Embodiment 2

[0024] Preparation of 5-ethoxy-7-chloro-[1,2,4]-triazolo-[1,5-C]-pyrimidine-2(3H)thione

[0025] Add 10.8g (0.048mol, 96% purity) 5-methoxy-7-chloro-[1,2,4]-triazolo-[4,3-C]-pyrimidine-3(2H)thione Into 40g ethanol. At 0°C-10°C, 5.4 g of sodium ethoxide was added to the above solution. The mixture was stirred at 0°C-10°C for 2h. Then the mixture was acidified with 9.5g of 36% concentrated hydrochloric acid, 50g of water was added, and the mixture was stirred at below -5°C for 30min and filtered. The filter cake was washed with 20ml of cold water and 20ml of cold ethanol and dried to obtain 9.5g of the target compound. The product was an off-white solid.

Embodiment 3

[0027] Preparation of 5-ethoxy-8-fluoro-[1,2,4]-triazolo-[1,5-C]-pyrimidine-2(3H)thione

[0028] Add 10.0g (0.048mol, 96% purity) 5-methoxy-8-fluoro-[1,2,4]-triazolo-[4,3-C]-pyrimidine-3(2H)thione Into 40g ethanol. At 0°C-10°C, 5.4 g of sodium ethoxide was added to the above solution. The mixture was stirred at 0°C-10°C for 2h. Then the mixture was acidified with 9.5g of 36% concentrated hydrochloric acid, 50g of water was added, and the mixture was stirred at -5°C for 30min, then filtered, and the filter cake was washed with 20ml of cold water and 20ml of cold ethanol and dried to obtain 9.2g of the target compound, which was an off-white solid.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of a triazolopyrimidine sulfydryl type compound. The method comprises the following steps: rearranging and substituting the compound as shown in formula (II) under alcohol-alkali action to obtain the triazolopyrimidine sulfydryl type compound as show in formula (I). The method disclosed by the invention expands a way and a material resource of the existing preparation method, does not produce environment-unfriendly byproducts and has an industrial application value.

Description

Technical field [0001] The invention relates to the synthesis of organic heterocyclic compounds, in particular to the preparation method of triazolopyrimidine sulfhydryl compounds. technical background [0002] The triazolopyrimidine sulfhydryl compound (I) is an important intermediate for preparing triazolopyrimidine sulfonamide herbicides. [0003] [0004] US6162915 and US5488109 disclose a method for preparing triazolopyrimidine sulfhydryl compounds. For example, the compound (V) is prepared by reacting the compound of formula (IV) with sodium ethoxide. [0005] [0006] Although this method has a high conversion rate, a large amount of malodorous methyl mercaptan (VI) is produced during the reaction, which poses serious environmental problems. Summary of the invention [0007] After in-depth research in the present invention, it is found that the compound represented by formula (II) can react with alcohol base to prepare the compound represented by formula (I). Since this meth...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 胡俊铎赖玉龙刘维郭群震虞小华蔡国平陈邦池
Owner ORIENTAL LUZHOU AGROCHEM