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A kind of synthetic method of isothiourea catalyst

A synthetic method and technology of isothiourea, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of toxicity and low yield of multi-step synthesis , to achieve the effects of wide application prospects, high yield, and mild reaction conditions

Active Publication Date: 2021-06-25
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0025] In J.Org.Chem., 2009,74,8309-8313, benzothiazole is used as a raw material, and under the condition of lithium tert-butoxide, carbon tetrachloride is used as a chlorine source, and DMF is used as a solvent to react to generate compound 7. To poisonous carbon tetrachloride, and the yield is not high as a multi-step synthesis

Method used

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  • A kind of synthetic method of isothiourea catalyst
  • A kind of synthetic method of isothiourea catalyst
  • A kind of synthetic method of isothiourea catalyst

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Embodiment 1

[0061] The synthesis of embodiment 1 compound 2 (o-nitrophenyl tert-butyl sulfide)

[0062] 2.8g (0.02mol) of o-fluoronitrobenzene (compound 1) was dissolved in 40ml of DMF solvent, 4.3g (0.03mol) of potassium carbonate solid was added, the temperature was raised to 80°C, and 2.0g (0.022mol) of tert-butyl Thiol, continue to react for 2h. After the reaction was completed, 100 ml of water and 100 ml of dichloromethane were added for extraction, and the organic phase was washed twice with 100 ml of water. The organic phase was concentrated to obtain 4.2 g (0.0199 mol) of compound 2 (o-nitrophenyl tert-butyl sulfide), with a yield of 99%. ( 1 H NMR (400MHz, CDCl 3 )δ7.71(dd, J=7.6,1.5Hz,1H),7.66(dd,J=7.7,1.6Hz,1H),7.49(dqd,J=15.0,7.5,1.6Hz,2H),1.31(s ,9H)).

Embodiment 2

[0063] The synthesis of embodiment 2 compound 3 (o-aminophenyl tert-butyl sulfide)

[0064] 4.2 g (0.0199 mol) of compound 2 (o-nitrophenyl tert-butyl sulfide) was dissolved in methanol, under nitrogen protection, 400 mg of Raney nickel was added, under hydrogen, reacted at normal temperature and pressure for 4 hours, suction filtered, and the filtrate was concentrated to obtain 3.4 g (0.0188mol) compound 3 (o-aminophenyl tert-butyl sulfide), yield 94%.

Embodiment 3

[0065] The synthesis of embodiment 3 compound 4 (o-aminophenyl tert-butyl sulfoxide)

[0066] 1.8g (0.01mol) of compound 3 (o-aminophenyl tert-butyl sulfide) was dissolved in 20ml of dichloromethane solution, cooled to -10°C, m-CPBA solution (2.1g (0.012mol) dissolved in 20ml of dichloromethane Chloromethane), after the dropwise addition, reacted for half an hour, suction filtered, the filtrate was washed twice with 40ml saturated sodium sulfite, and washed once with 40ml saturated sodium carbonate. The organic phase was dried and concentrated over sodium sulfate, and separated on a silica gel column (petroleum ether: ethyl acetate = 4:1) to obtain 1.8 g (0.009 mol) of compound 4 (o-aminophenyl tert-butyl sulfoxide), with a yield of 90%. ( 1 H NMR (400MHz, CDCl 3 )δ7.24–7.17(m,1H),7.10(d,J=7.0Hz,1H),6.71(t,J=7.5Hz,1H),6.63(d,J=8.2Hz,1H),5.15( s,2H),1.31(s,9H). 13 C NMR (100MHz, CDCl 3 )δ149.4, 131.8, 128.8, 117.9, 117.5, 116.4, 58.8, 23.5. HRMS (ESI) m / z calcd for C 10 h...

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Abstract

The invention relates to the field of organic chemistry, in particular to a synthesis method of an isothiourea catalyst. The steps include: (1) using o-fluoronitrobenzene as a starting material, and tert-butyl mercaptan to synthesize o-nitrophenyl tert-butyl sulfide under alkali-catalyzed conditions; (2) o-nitrobenzene tert-butyl sulfide Ether hydrogenation reaction generates o-aminophenyl tert-butyl sulfide; (3) o-aminophenyl tert-butyl sulfide is oxidized to obtain o-aminophenyl tert-butyl sulfoxide; (4) o-aminophenyl tert-butyl sulfoxide and iso The cyano-p-toluenesulfonate propyl ester compound is reacted to prepare an isothiourea organic catalyst. The method of the present invention utilizes a multi-component reaction to efficiently convert three functional groups into a new functional group without metals; each step has a high yield, atom economy, less pollution, simple operation, and low cost. The reaction condition is mild, suitable for batch industrial production, and has broad application prospects.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for synthesizing an organic catalyst, especially a method for synthesizing an isothiourea catalyst. Background technique [0002] Organic catalysts are used to catalyze organic reactions, and have the advantages of mild reaction conditions, high yields, and fast reaction speeds. Therefore, it is very important to develop high-efficiency organic catalysts, especially organic catalysts that are widely used. Isothiourea organic catalysts play a relatively good catalytic role in the synthesis of chiral synthesis, esterification, carbon acylation, and heterocycles, and play a very important role in the synthesis of active pharmaceuticals and pesticides. [0003] Org. Lett., 2006, 10, 1351-1354 found that BTM (CAS: 885051-07-0) has an outstanding effect in the kinetic resolution of secondary benzyl alcohol, and can enantioselectively catalyze the acyl group of sila...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04B01J31/02
CPCB01J31/0235C07D513/04
Inventor 孙智华吴圣峰戴伊如
Owner SHANGHAI UNIV OF ENG SCI
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