Preparation method of 2-pyrrole benzenylsulfonylamide compound

A technology for pyrrole sulfonamides and compounds, which is applied in the field of preparation of 2-pyrrole sulfonamide compounds, can solve the problems of poor selectivity, low operation yield, and easy production of by-products, etc., achieving good yield and safety for operators , Environmentally friendly effect

Inactive Publication Date: 2010-09-01
山东兴安智慧科技有限公司
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  • Application Information

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Problems solved by technology

Among them, 2-pyrrole sulfonamide compounds have gradually attracted people's attention because of their unique structure, but so far there are few reports on the synthesis method of 2-pyrrole sulfonamide compounds, mainly through pyrrole and sulfonamide compounds on copper It is prepared by reaction under the action of a catalyst, but the yield of this operation is low, and by-products are easily produced, and the selectivity is not good, so the application of this type of compound is limited

Method used

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  • Preparation method of 2-pyrrole benzenylsulfonylamide compound
  • Preparation method of 2-pyrrole benzenylsulfonylamide compound
  • Preparation method of 2-pyrrole benzenylsulfonylamide compound

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preparation example Construction

[0025] The preparation method of benzenesulfonylimide compound:

[0026] Taking N-benzylidene-4-methylbenzenesulfonamide as an example, the preparation method is: 1mmol benzaldehyde (reactant A) and 1mmol 4-methylbenzenesulfonamide (reactant B), and 0.5mmol chloride Mix aluminum, grind and react at room temperature for 1.5 hours, after the reaction, add 20ml of saturated aqueous sodium chloride solution, extract with ethyl acetate, take the organic layer and dry it with anhydrous sodium sulfate and filter, take the filtrate and distill off the solvent, N-benzylidene-4-methylbenzenesulfonamide was obtained by recrystallization from ethanol.

[0027] The benzenesulfonylimide compounds used in the examples were prepared according to the above method steps, the difference was that the raw materials were changed, wherein reactant A and reactant B were shown in Table 1 below:

[0028] Table 1

[0029] Benzenesulfonylimides

Embodiment 1

[0031] N-(Phenyl(2-pyrrole)methyl)p-toluenesulfonamide

[0032]

[0033] Pyrrole (13.4mg, 0.2mmol), N-benzylidene-4-methylbenzenesulfonamide (103.6mg, 0.4mmol), indium trichloride (0.02mmol), methanesulfonic acid (0.04mmol) in tetrahydrofuran (0.6mL), reacted in an ice-water bath, detected the end point of the reaction with TLC, and reacted for 8 hours. After the reaction was completed, 5mL of water was added to the reaction solution, extracted with 20mL of dichloromethane, the organic layer was dried and filtered, and the filtrate was distilled to remove the solvent. Afterwards, column chromatography (petroleum ether: ethyl acetate = 3: 1) was refined, and TLC tracked and collected the eluent with an Rf value of 0.25 to 0.28, and the collected eluent was decompressed to remove the eluent to obtain the target product 40.5 mg, yield 62%, yellow solid.

[0034] 1 MR (500MHz, CDCl 3 ): δ8.59(s, 1H), 7.54-7.57(m, 2H), 7.18-7.23(m, 3H), 7.13-7.15(d, J=7.5Hz, 2H), 7.09-7.12(m,...

Embodiment 2

[0036] Refer to Example 1 for the operation, without adding indium trichloride, the others are the same as Example 1, and the yield is 8%.

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Abstract

The invention discloses a preparation method of 2-pyrrole benzenylsulfonylamide compounds as shown in formula (III), and the method comprises the following steps: pyrrole as shown in formula (I) and phenylsulfonyl imine compounds as shown in formula (II) react completely in an inert organic solvent under the function of metal catalyst of indium trichloride at minus 10-10DEG C, the reaction endpoint is detected by TLC, and after the reaction is finished, the reaction solution is processed, thus preparing the 2-pyrrole benzenylsulfonylamide compounds as shown in formula (III); and the amount ratio of the pyrrole as shown in formula (I) to the phenylsulfonyl imine compounds as shown in formula (II) is 1:1.0-4.0. The method has the advantages of mild reaction condition, simple operation and high yield; being environmental-friendly, generating no toxicity basically in the whole production process, being safe to operators, generating no by-products as all atoms of raw materials participate in the product composition, being consistent with economic principle and having high raw material utilization ratio.

Description

(1) Technical field [0001] The invention relates to a preparation method of 2-pyrrole sulfonamide compounds. (2) Background technology [0002] Pyrrole and its derivatives are important intermediates for the synthesis of drugs, pigments, etc. , but also an important component of many natural and non-natural compounds (Tetrahedron1997, 53, 7731; Tetrahedron 1998, 54, 5075; J.Am.Chem.Soc.1999, 121, 54). Among them, 2-pyrrole sulfonamide compounds have gradually attracted people's attention because of their unique structure, but so far there are few reports on the synthesis method of 2-pyrrole sulfonamide compounds, mainly through pyrrole and sulfonamide compounds on copper It is prepared by reaction under the action of a catalyst, but the yield of this operation is low, and by-products are easily produced, and the selectivity is not good, so the application of this type of compound is limited. (3) Contents of the invention [0003] The technical problem to be solved by the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/335B01J31/26
Inventor 崔冬梅金卫波
Owner 山东兴安智慧科技有限公司
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