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

2-sulfohydantoin as well as preparation method and application thereof

A technology of thiohydantoin and p-nitrophenyl, which is applied in the field of sulfur-substituted heterocyclic compounds and heterocyclic compounds, can solve problems that have not been seen, and achieve the effect of easy portability and fast detection process

Inactive Publication Date: 2013-02-13
SOUTHERN MEDICAL UNIVERSITY
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its application in anion recognition has not been seen

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
  • 2-sulfohydantoin as well as preparation method and application thereof
  • 2-sulfohydantoin as well as preparation method and application thereof
  • 2-sulfohydantoin as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1. Compound Preparation

[0033] 3.62 g of 4-hydroxyphenylglycine methyl ester and 3.82 g of n-butyl isothiocyanate were added to a 100 mL flask, and then 30 mL of tetrahydrofuran was added. After reacting at room temperature for 12 hours, the solvent was distilled off under reduced pressure, and the residual solid was purified by a silica gel column with the composition of ethyl acetate:n-hexane=1:1 (v / v) to obtain 4.44 g of white solid. Yield 84%.

[0034] 2. Compound Characterization

[0035] Mp 291-292°C.

[0036] 1 H NMR (400MHz,THF-d 8 ):δ0.83~0.87(m,3H,CH3),1.09~1.24(m,4H,CH2CH2),3.42~3.56(m,2H,CH2),5.28(s,1H,CH),6.70~6.73( d,2H,Ar),7.53~7.55(d,2H,Ar),8.59(s,1H,OH),10.09(s,1H,NH).

[0037] 13 C NMR (100MHz,THF-d 8 ): δ13.08, 19.69, 29.24, 40.38, 61.44, 114.66, 121.75, 128.46, 158.54, 171.76, 182.36.

[0038] IR (cm -1 ,KBr):3263,3014,2362,2106,1588,1525,1409,1334,1251,1179,1013,930,843,735,698.

[0039] Anal. Calcd for C 13 h 16 N 2 o 2 S:C,59.07;H...

Embodiment 2

[0063] 4-(4’-Hydroxyphenyl)1-(4’-nitrophenyl)-2-thiohydantoin

[0064] 1. Preparation of 4-(4'-hydroxyphenyl)1-(4'-nitrophenyl)-2-thiohydantoin

[0065] Add 3.62 g (20 mmol) of 4-hydroxyphenylglycine methyl ester and 3.60 g (20 mmol) of p-nitrophenyl isothiocyanate into a 100 mL flask, and then add 40 mL of tetrahydrofuran. After reacting at room temperature for 10 hours, the solvent was distilled off under reduced pressure, and the residual solid was purified with a silica gel column under the condition that the eluent composition was ethyl acetate:n-hexane=1:2 (v / v) to obtain 5.40 g of white solid. Yield 82%.

[0066] 2. Characterization of 4-(4’-hydroxyphenyl)1-(4’-nitrophenyl)-2-thiohydantoin

[0067] 1 H NMR (400MHz, DMSO-d 6 ):δ5.47(s,1H,CH),6.70~6.73(d,2H,Ar),6.92~6.93(d,2H,Ar),7.64~7.66(d,2H,Ar),8.02~8.04( d, 2H Ar), 8.62 (s, 1H, OH), 10.21 (s, 1H, NH).

[0068] 13 C NMR (100MHz, DMSO-d 6 ): δ67.34, 114.66, 121.75, 123.71, 127.88, 128.46, 131.33, 147.55, 157.54...

Embodiment 3

[0077] 4-(4’-Hydroxyphenyl)1-(4’-cyanophenyl)-2-thiohydantoin

[0078] 1. Preparation of 4-(4'-hydroxyphenyl)1-(4'-cyanophenyl)-2-thiohydantoin

[0079] Add 3.62 g (20 mmol) of 4-hydroxyphenylglycine methyl ester and 3.20 g (20 mmol) of p-cyanophenyl isothiocyanate into a 100 mL flask, and then add 50 mL of tetrahydrofuran. After reacting at room temperature for 24 hours, the solvent was distilled off under reduced pressure, and the residual solid was purified by a silica gel column with the composition of ethyl acetate:n-hexane=1:3 (v / v) to obtain 5.32 g of white solid. Yield 86%.

[0080] 2. Characterization of 4-(4’-hydroxyphenyl)1-(4’-cyanophenyl)-2-thiohydantoin

[0081] 1 H NMR (400MHz, DMSO-d 6 ):δ5.52(s,1H,CH),6.67~6.69(d,2H,Ar),6.87~6.90(d,2H,Ar),7.53~7.55(d,2H,Ar),7.99~8.01( d, 2H, Ar), 8.55 (s, 1H, OH), 9.31 (s, 1H, NH).

[0082] 13 C NMR (100MHz, DMSO-d 6 ): δ63.44, 114.61, 122.15, 123.33, 127.92, 128.36, 133.48, 146.15, 157.04, 172.78, 180.22.

[0083] Th...

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 relates to a sulfur-containing heterocyclic compound. The compound is 2-sulfohydantoin; a chemical structure of the 2-sulfohydantoin is shown in a formula (I) in the specification; and in the formula (I), R is one of C1-12 alkyl, p-nitrophenyl, p-cyano phenyl, p-methoxyphenyl, p-butyl phenyl, 3,5-di(trifluoromethyl)phenyl and phenyl. The 2-sulfohydantoin is obtained by reacting isothiocyanate with para hydroxy phenylglycine methyl ester, has an anion recognition performance, and can be used for detecting fluorinion.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to heterocyclic compounds, in particular to sulfur-substituted heterocyclic compounds. Background technique [0002] Anion recognition refers to the process in which receptors (subjects) selectively bind to anions and produce a specific function. It plays a pivotal role in the fields of biology, chemistry, medicine, catalysis and environmental science, especially in the metabolic process of organisms. Such as DNA recognition, molecular transport, etc. play an important role. The research on anion recognition and sensing system has gradually become a research hotspot in supramolecular chemistry. Jiang Hong and others designed and synthesized the anion recognition receptor N-nitrourea, added fluoride ion, dihydrogen phosphate ion, and hydrogen phosphate ion to the DMSO solution of the receptor, and the color of the solution changed from yellow to purple, so as to realize the recognition...

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
IPC IPC(8): C07D233/86C09K9/02G01N21/78
Inventor 刘瑞源勇雪瞿金清严轶琛游文玮
Owner SOUTHERN MEDICAL UNIVERSITY
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