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N-sulfuryl ketimine compounds and preparation method thereof

A technology of sulfonyl imide and sulfonamide, which is applied in the preparation of sulfonic acid amide, chemical instruments and methods, organic compound/hydride/coordination complex catalyst, etc. products, limited applicability, etc., to achieve the effects of convenient operation, mild reaction conditions and good product quality

Inactive Publication Date: 2008-12-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some preparation methods have cumbersome steps and are prone to generate by-products, and some have low yields and poor reproducibility, thus limiting their applicability

Method used

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  • N-sulfuryl ketimine compounds and preparation method thereof
  • N-sulfuryl ketimine compounds and preparation method thereof
  • N-sulfuryl ketimine compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] N-(1-(4-ethylphenyl)ethylidene)benzenesulfonamide:

[0023]

[0024] P-ethylphenylacetylene (195.3mg, 1.5mmol), benzenesulfonamide (78.6mg, 0.5mmol), gold chloride complex ((PPh) 3 AuCl) (5 mg, 0.01 mmol), silver trifluoromethanesulfonate (10 mg, 0.04 mmol) were mixed in tetrahydrofuran (2.0 mL), heated in an oil bath at 100° C. for 6 h. Cool to room temperature, add saturated NaHCO 3 , and then extracted with ethyl acetate (50mL × 3), the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and column chromatography (petroleum ether: ethyl acetate = 20: 1) gave 77 mg of the target compound with a yield of 53.6 %, yellow oily liquid.

[0025] 1 H NMR (500MHz, CDCl 3 ): δ8.06-8.03(m, 2H), 7.84(d, J=8.5Hz, 2H), 7.60-7.54(m, 3H), 7.23(d, J=8.5Hz, 2H), 2.98(s, 3H), 2.68(q, J=7.5Hz, 2H), 1.23(t, J=7.5Hz, 3H).

Embodiment 2

[0027] N-(1-(4-ethylphenyl)ethylidene)-4-iodobenzenesulfonamide:

[0028]

[0029] The operation was referred to Example 1, except that p-iodobenzenesulfonamide was used instead of benzenesulfonamide to obtain 130 mg of the target product as a yellow oily liquid with a yield of 63%.

[0030] 1 H NMR (500MHz, CDCl 3 ): δ7.90(d, J=8.0Hz, 2H), 7.83(d, J=8.0Hz, 2H), 7.75(d, J=8.0Hz, 3H), 7.24(d, J=8.0Hz, 2H ), 2.97(s, 3H), 2.69(q, J=7.5Hz, 2H), 1.23(t, J=7.5Hz, 3H).

Embodiment 3

[0032] 4-iodo-N-(1-(4-methoxyphenyl)ethylidene)benzenesulfonamide:

[0033]

[0034] The operation refers to Example 1, except that p-methoxyphenylacetylene is replaced by p-ethylphenylacetylene, p-iodobenzenesulfonamide is replaced by benzenesulfonamide, tetrahydrofuran is replaced by toluene, and 207 mg of the target product is obtained with a yield of 99.7%, a yellow oily liquid .

[0035] 1 H NMR (500MHz, CDCl 3 ): δ7.92-7.89(m, 4H), 7.75(d, J=8.5Hz, 2H), 6.90(d, J=9.0Hz, 2H), 3.87(s, 3H), 2.95(s, 3H) .

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PUM

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Abstract

The invention discloses an N-sulfonylketimine compound and the preparation method thereof. The preparation method includes that alkine compound shown in formula (I) and a sulfonamide compound shown in formula (II) react in the presence of a MLYn transition metal catalyst in an inert organic solvent at 35-140 DEG C; and the reaction solution is subjected to a post-treatment to obtain the N-sulfonylketimine compound shown in formula (III). The method has the advantages that the reaction conditions is mild; the operation is convenient; the product quality is good; the yield is high; the environment friendliness is ensured; the whole production process is substantially harmless; and the operators are safe; the reaction is in accordance with the atom economic principle and has high utilization rate of the raw material. Since the N-sulfonylketimine is an excellent raw material for preparing pharmaceuticals, agricultural chemicals and chemical products, the preparation method has wide industrial application prospect.

Description

(1) Technical field [0001] The invention relates to N-sulfonylketimine compounds and a preparation method thereof. (2) Background technology [0002] As important chemical raw material intermediates, N-sulfonylketimine compounds are widely used in the synthesis fields of pesticides and medicines. There are many reports about the synthetic method of N-sulfonyl ketimine compounds so far: 1. It is prepared by condensation and dehydration of ketones with sulfenamides under Lewis acid conditions, and then further oxidation (Yang, Qin, Angew. Chem. Int. Ed. (2006), 45(23), 3832-3835.; Ruano, Jose Luis Garcia, Org. Synth. (2007), 84, 129-138; Ruano, Jose Luis Garcia, Org. Let. (2005), 7(2), 179-182). 2. Prepared by oxidative addition of ketones and styrene under palladium catalysis (Timokhin, Vitaliy I., J.Am.Chem.Soc.(2003), 125(43), 12996-12997; Brice, Jodie L , J. Am. Chem. Soc. (2005), 127(9), 2868-2869;). 3. Prepared by direct dehydration condensation of sulfonamides and k...

Claims

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Application Information

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IPC IPC(8): C07C311/15C07C303/40B01J31/24B01J31/28
Inventor 崔冬梅郑金洲
Owner ZHEJIANG UNIV OF TECH
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