Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing N-methyl-N-(3-methyl phenyl) thiocarbamate-2-naphthyl

A technology of thiocarbamic acid and methyl phenyl, which is applied in organic chemistry and other fields, and can solve problems such as restrictions on industrial production and safety issues

Active Publication Date: 2015-02-11
四川摩尔生物制药有限公司
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process uses toxic and harmful thiophosgene. At present, the production, transportation and use of thiophosgene are strictly controlled in China, which limits the industrial production of this technology; 2. An alternative method for tolnaftate, Ayyangar, N.R.et al, Organic Preparations and Procedures International, 22(1), 128-30; 1990, the literature reports that N-methyl-3-methylaniline reacts with carbon disulfide, and feeds chlorine gas to generate an active intermediate, which is then reacted with 2-naphthol Reaction to obtain the target product; this technology uses highly toxic chlorine gas, which brings serious environmental protection and safety problems to production
[0003] The use of thiophosgene or chlorine is unavoidable in the prior art. These reagents are under the compulsory control of the state, and their production, transportation and use involve serious safety and environmental issues.

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
  • Method for preparing N-methyl-N-(3-methyl phenyl) thiocarbamate-2-naphthyl
  • Method for preparing N-methyl-N-(3-methyl phenyl) thiocarbamate-2-naphthyl
  • Method for preparing N-methyl-N-(3-methyl phenyl) thiocarbamate-2-naphthyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A preparation method of compound N-methyl-N-(3-methylphenyl)thiocarbamate-2-naphthyl ester as shown in formula E, is characterized in that: the method comprises the following steps:

[0033] 1) Preparation of compound N-methyl-N-(3-methylphenyl) formamide shown in formula B

[0034] Take 20g of the compound N-methyl-3-methylaniline shown in formula A and 1.0g of active zinc powder, add it into a 100ml three-necked flask, add 22ml of formic acid dropwise under stirring, and control the temperature at 40°C. After the dropwise addition, Raise the temperature to reflux reaction, then lower to room temperature after completion, add 50ml of dichloromethane, filter, wash with a small amount of dichloromethane, combine the organic phase, wash the organic phase twice with water, twice with saturated sodium bicarbonate solution, and twice with saturated brine Once concentrated under reduced pressure, 23g of compound N-methyl-N-(3-methylphenyl)formamide as shown in formula B was o...

Embodiment 2

[0046] A preparation method of compound N-methyl-N-(3-methylphenyl)thiocarbamate-2-naphthyl ester as shown in formula E, is characterized in that: the method comprises the following steps:

[0047] 1) Preparation of compound N-methyl-N-(3-methylphenyl) formamide shown in formula B

[0048] Take 19g of the compound N-methyl-3-methylaniline shown in formula A, add 30g of toluene into a 50ml three-necked flask, stir, add 8.8g of formic acid dropwise at room temperature, after the dropwise addition, heat up to reflux for reaction, and the reaction is complete Then it was cooled to room temperature, washed with water to neutrality, and the solvent was recovered to obtain 21 g of compound N-methyl-N-(3-methylphenyl)formamide shown in formula B;

[0049]

[0050] 2) Preparation of compound N-methyl-N-(3-methylphenyl) thioformamide shown in formula C

[0051] Take 21g of the compound N-methyl-N-(3-methylphenyl)formamide shown in formula B, and add 50ml of toluene into a 200ml three-...

Embodiment 3

[0060] A preparation method of compound N-methyl-N-(3-methylphenyl)thiocarbamate-2-naphthyl ester as shown in formula E, is characterized in that: the method comprises the following steps:

[0061] 1) Preparation of compound N-methyl-N-(3-methylphenyl) formamide shown in formula B

[0062] Take 19g of the compound N-methyl-3-methylaniline shown in formula A, add 30g of toluene into a 50ml three-necked flask, stir, add 8.8g of formic acid dropwise at room temperature, after the dropwise addition, heat up to reflux for reaction, and the reaction is complete Then it was cooled to room temperature, washed with water to neutrality, and the solvent was recovered to obtain 21 g of compound N-methyl-N-(3-methylphenyl)formamide shown in formula B;

[0063]

[0064] 2) Preparation of compound N-methyl-N-(3-methylphenyl) thioformamide shown in formula C

[0065] Take 21g of the compound N-methyl-N-(3-methylphenyl)formamide shown in formula B, and add 50ml of toluene into a 200ml thre...

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 method for preparing N-methyl-N-(3-methyl phenyl) thiocarbamate-2-naphthyl. By adopting the method, usage of harmful and toxic thiophosgene or chlorine can be avoided, and physical health of staff can be protected. The method is suitable for large-scale industrial production and application, and good enterprise benefits and social benefits can be obtained.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a preparation method of N-methyl-N-(3-methylphenyl)thiocarbamate-2-naphthyl ester. Background technique [0002] The synthetic technology of the currently disclosed N-methyl-N-(3-methylphenyl) thiocarbamate-2-naphthyl ester has: Aniline reacts with thiophosgene to generate an active intermediate, which then reacts with 2-naphthol; or 2-naphthol reacts with thiophosgene to generate an active intermediate, which then reacts with N-methyl-3-methanol Aniline reaction gives the product. This process uses toxic and harmful thiophosgene. At present, the production, transportation and use of thiophosgene are strictly controlled in China, which limits the industrial production of this technology; 2. An alternative method for tolnaftate, Ayyangar, N.R.et al, Organic Preparations and Procedures International, 22(1), 128-30; 1990, the literature reports that N-methyl-3-methylaniline reacts wi...

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): C07C333/08C07C327/06
Inventor 蔡泽贵孟雄李远志
Owner 四川摩尔生物制药有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com