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Preparation method of N,N-disubstituted sulfonamide compound

A technology of sulfonamide and ether compounds, applied in the field of N, can solve the problems of limited application range, harsh conditions, expensive raw materials, etc., and achieve the effects of wide industrial application prospects, mild reaction conditions, and convenient operation

Active Publication Date: 2012-04-11
特康药业集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many defects in the above-mentioned preparation method: expensive raw materials are difficult to obtain, the scope of application is not wide, the limitations are large, the operation steps are cumbersome, and the conditions are harsh, thus limiting its applicability

Method used

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  • Preparation method of N,N-disubstituted sulfonamide compound
  • Preparation method of N,N-disubstituted sulfonamide compound
  • Preparation method of N,N-disubstituted sulfonamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: N-p-toluenesulfonyl tetrahydropyrrole (I-1)

[0019] Mix 171.3mg (1mmol) of p-toluenesulfonamide (III-1) and 0.32ml (4mmol) of tetrahydrofuran, in 2ml of toluene, under the action of 20μl (0.2mmol) of trifluoromethanesulfonic acid, stir the reaction at 170℃18 After the reaction was completed, the reaction solution was distilled to remove the solvent, and then column chromatography (eluent: petroleum ether: ethyl acetate = 5:1), TLC followed to collect the eluent with Rf value of 0.3~0.35 The collected eluent was distilled under reduced pressure and dried to obtain 220.8 mg of target compound (I-1), with a yield of 98.1%, a white solid.

[0020] 1 H NMR(500MHz, CDCl 3 ): δ1.76-1.73(m, 4H), 2.43(s, 3H), 3.14-3.21(m, 4H), 7.32(d, 2H, J=8.5Hz), 7.71(d, 2H, J=8.5 Hz).

[0021]

Embodiment 2

[0023] The amount of tetrahydrofuran was increased to 2ml (25mmol), other operations were the same as in Example 1, and the yield was 96.6%.

Embodiment 3

[0025] The reaction temperature was changed to 30°C, the reaction time was 48 hours, the other operations were the same as in Example 1, and the yield was 3%.

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PUM

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Abstract

The invention discloses a preparation method of N,N-disubstituted sulfonamide compounds, which comprises the following steps: mixing sulfonamide compounds and ether compounds in a solvent, reacting at 30-200 DEG C for 1-48 hours under the action of a protonic acid catalyst, after the reaction, performing post-treatment of the reaction solution to obtain the N,N-disubstituted sulfonamide compounds as shown in formula (I); the protonic acid catalyst is trifluoromethanesulfonic acid, sulfuric acid, trifluoroacetic acid, p-toluenesulfonic acid, or methanesulfonic acid; the solvent is toluene, xylene, acetonitrile, cyclohexane, water, dimethyl sulfoxide, dimethyl formamide, or dioxane; the beneficial effects of the present invention are mainly reflected in that: (1) the reaction condition is mild; the operation is convenient; and the yield is high; (2) a protonic acid is used as a catalyst, which is environment-friendly; sulfonamide compounds are important organic intermediates, and are very good raw materials for the synthesis of medicine intermediates, pesticides, and chemical products, so the invention has wide industrial application prospects.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing an intermediate, in particular to a method for preparing an N,N-disubstituted sulfonamide compound. (2) Background technology [0002] Sulfonamide compounds are also important chemical raw materials and organic synthesis intermediates, which are widely used in the fields of medicine and pesticides. There are few reports on the synthesis of N-substituted sulfonamide compounds so far: one is prepared by the reaction of sulfonyl chloride and amine in water or organic solvents (Kamal Ahmed, Reddy J. Surendranadha, Bharathi E. Vijaya, Dastagiri D, Tetrahedron) Lett (2008), 49, 348). The second method is prepared by two-step reaction with sodium sulfinate as raw material and azo dicarboxylic acid bis(2,2,2-trichloroethyl) (Chan WingYan, Berthelette Carl, Tetrahedron Lett (2002) , 43, 4537). Three is synthesized with sulfonate amine salt as raw material, and melamine chloride under alkaline conditions of tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/04C07D295/26C07D207/48C07C303/40C07C311/21
Inventor 崔冬梅柏春美戚兰君张成柱
Owner 特康药业集团有限公司
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