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Synthetic method of dialkyl amino dithiocarbamate alkyl ester

A technology of alkyl dialkylaminodithiocarbamate and sodium phenethylaminodithiocarbamate, applied in organic chemical methods, sulfide preparation, organic chemistry, etc., can solve problems that have not been reported in the literature

Active Publication Date: 2020-01-14
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] As far as we know, there is no similar literature report with this application

Method used

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  • Synthetic method of dialkyl amino dithiocarbamate alkyl ester
  • Synthetic method of dialkyl amino dithiocarbamate alkyl ester
  • Synthetic method of dialkyl amino dithiocarbamate alkyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Add benzyltrimethylammonium trifluoromethanesulfonate (1.0 mmol), N,N-diethylcarbamate sodium (2.0 mmol), CuI ( 5 mol% relative to benzyltrimethylammonium trifluoromethanesulfonate), acetonitrile (3 mL), and finally the ground-mouth test tube was sealed with a rubber stopper. The test tube was placed in an 80°C oil bath and stirred for 18 hours. Then, the reaction mixture was cooled to room temperature, quenched with 15 mL of saturated NaCl solution, and extracted with ethyl acetate (3 x 20 mL). And the combined organic layers were dried over anhydrous magnesium sulfate, then adsorbed onto some silica gel under reduced pressure on a rotary evaporator. Transfer the silica gel with adsorbed sample to a silica gel column. After purification by silica gel column chromatography (petroleum ether: ethyl acetate = 20:1 as eluent), yellow oily liquid N,N-diethylcarbamate benzyl ester was obtained with a yield of 95%. The reaction equation is shown below.

[0012]

[0013]...

Embodiment 2

[0018] (o-methylbenzyl)trimethylammonium trifluoromethanesulfonate instead of benzyltrimethylammonium trifluoromethanesulfonate in Example 1 to obtain yellow oily liquid N,N-diethylaminodithioformic acid The yield of (2-methylbenzyl)ester was 95%.

[0019] 1 H NMR (400MHz, CDCl 3 )δ7.28(dd,J=7.2,1.6Hz,1H),7.16–7.03(m,3H), 4.41(s,2H),3.97(q,J=7.1Hz,2H),3.63(q,J =7.1Hz, 2H), 2.32(s, 3H), 1.19(dd, J=12.9, 5.8Hz, 6H).

[0020] 13 C NMR (101MHz, CDCl 3 )δ195.42, 137.44, 133.34, 130.48, 130.45, 127.90, 126.19, 49.26, 46.69, 40.83, 19.34, 12.43, 11.60.

[0021] MS(EI):m / z(%)=253(50)[M] + ,220(5),148(100),105(90),88(40).

Embodiment 3

[0023] (m-methylbenzyl)trimethylammonium trifluoromethanesulfonate instead of benzyltrimethylammonium trifluoromethanesulfonate in Example 1 to obtain yellow oily liquid N,N-diethylaminodithioformic acid The yield of (3-methylbenzyl)ester was 92%.

[0024] 1 H NMR (400MHz, CDCl 3 )δ7.24–7.06(m,3H),7.05–6.90(m,1H),4.42(s,2H),3.97(q,J=7.0Hz,2H),3.65(q,J=7.2Hz,2H ),2.26(s,3H),1.20(q,J=5.9, 5.2Hz,6H).

[0025] 13 C NMR (101MHz, CDCl 3 )δ195.39, 138.29, 135.76, 130.15, 128.52, 128.30, 126.48, 49.43, 46.74, 42.33, 21.38, 12.51, 11.63.

[0026] MS(EI):m / z(%)=253(60)[M] + ,207(10),148(100),105(70),88(55).

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Abstract

In organic sulfur compounds, dialkyl amino dithiocarbamate alkyl ester plays a very important role. Researches show that dialkyl amino dithiocarbamate alkyl ester and the derivatives thereof have widebiological characteristics and pharmacological activity. For example, many studies show that the dialkyl amino dithiocarbamate alkyl ester has various activities, including anti-proliferative, anti-glaucoma, antibacterial, antifungal, breast cancer treatment and cholinesterase inhibition activities, and can be used as a myocardial imaging agent. It is known that dialkyl amino dithiocarbamate alkyl ester and the derivatives thereof can be taken as inhibitors of HIV-1 NCp7, antiviral agents, and non-flavonoid TRPV1 antagonists. Dialkyl amino dithiocarbamate alkyl ester has a wide application range, and is massively produced in the world. The invention provides a method for efficiently synthesizing dialkyl amino dithiocarbamate alkyl ester. Under the catalysis of CuI, a chiral quaternary ammonium salt and a dialkyl amino dithioformate are used for C-S cross coupling for the first time, and dialkyl amino dithiocarbamate alkyl ester is prepared. The target product is further converted andcoupled with brominated aromatic hydrocarbons to obtain high-purity enantiomer chiral thioethers. The synthesis process has the advantages of mild reaction conditions, wide universality, no toxicity or danger, high yield, wide substrate range and the like.

Description

technical field [0001] This patent relates to the research fields of organic synthesis, drug synthesis, and organic chemical industry. The specific method is to synthesize dialkylaminodisulfide in one step through C-S cross-coupling of alkyl quaternary ammonium salt and dialkylaminodithioformate Alkyl formate compounds. Background technique [0002] Dialkylcarbamate and its derivatives have a wide range of biological properties and pharmacological activities. Benzylcarbamate (such as 4-methoxybenzyl-N, N-diethylcarbamate) that exhibits excellent herbicidal activity against grasses and broad-leaved plants belongs to Dialkylaminodithiocarboxylates (S.Wakamori, Y.Yoshida, Y.Ishii, Agric.Biol.Chem.1969, 33, 1367–1376.) In addition, many studies have shown that dialkylamino Dithioformates also exhibit various biomedical activities, including antiproliferative (S.L.Cao, Y.Han, C.Z.Yuan, Y.Wang, Z.Xiahou, J.Liao, R.T.Gao, B.B.Mao, B.L.Zhao , Z.F.Li, X.Xu, Eur.J.Med.Chem.2013,64,...

Claims

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Application Information

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IPC IPC(8): C07C333/20C07C319/14C07C321/20
CPCC07B2200/07C07C319/14C07C333/20C07C321/20
Inventor 曾庆乐陈虹艺
Owner CHENGDU UNIVERSITY OF TECHNOLOGY
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