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
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its application in ani

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  • 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

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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...

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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

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Application Information

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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
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