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Preparation method of sulfonylurea and sulfonamide formate compounds

A compound and alkyl technology, applied in the preparation of sulfonic acid amides, chemical instruments and methods, compounds containing elements of Group 3/13 of the periodic table, etc., can solve the problems of unfriendly environment, poor safety and high cost

Active Publication Date: 2015-05-27
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The shortcoming of above-mentioned method is: (1) unfriendly to environment, safety is poor, and first two kinds of methods all need to use phosgene, and need comparatively strict reaction conditions such as anhydrous; (2) substrate universality is poor, sulfonamide group Formate ester compounds can only be prepared by the second method, and the first method can only prepare the corresponding sulfonylurea compounds of primary amines; (3) the third method has poor atom economy and high cost, and the intermediate benzene Oxycarbonamides are more expensive than raw amines, and the effective molecular weight is not high

Method used

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  • Preparation method of sulfonylurea and sulfonamide formate compounds
  • Preparation method of sulfonylurea and sulfonamide formate compounds
  • Preparation method of sulfonylurea and sulfonamide formate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] The preparation of embodiment 1N-morpholine base-N'-(4-methylbenzenesulfonyl)urea

[0089] Chemical name: N-morpholino-N’-(4-methylbenzenesulfonyl)urea

[0090] Molecular formula: C 12 h 16 N 2 o 4 S

[0091] CAS registration number: 10518-51-1

[0092]

[0093] method one:

[0094] Add Pd(OAc) in turn to the 25ml two-necked bottle 2(1mg, 0.004mmol), p-toluenesulfonyl azide (79mg, 0.40mmol), morpholine (42mg, 0.48mmol), acetonitrile 4ml, the system was evacuated to 20mmHg, then filled with CO gas to normal pressure, and so on 3 times. After the system was stirred vigorously at room temperature for 12 hours, the solvent was concentrated under reduced pressure, and the residue was separated and purified by column chromatography (dichloromethane: methanol (volume ratio) = 10:1) to obtain 111 mg of a white solid product with a yield of 93 %.

[0095] Method Two:

[0096] First add p-toluenesulfonyl chloride (76mg, 0.40mmol), sodium azide (34mg, 0.52mmol), acet...

Embodiment 2-36

[0101] Examples 2-36 were prepared by the same method as in Example 1, and the specific raw material ratios are shown in Table 1 and Table 2.

[0102] The concrete raw material ratio of the method one of table 1 embodiment 2-36

[0103]

[0104]

[0105] The concrete raw material ratio of the method two of table 2 embodiment 2-35

[0106]

[0107]

[0108] The product names, yields and characterization results of Examples 2-36 are listed in Table 3.

[0109] Product information and characterization of table 3 embodiment 2-36

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

Embodiment 37

[0117] Example 37 Preparation of 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-(4-methylbenzenesulfonyl)urea

[0118] Chemical name: 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-(4-methylbenzenesulfonyl)urea

[0119] Molecular formula: C 13 h 15 N 5 o 4 S

[0120] CAS registration number: 125069-22-9

[0121]

[0122] method one:

[0123] Add Pd(OAc) in turn to the 25ml two-necked bottle 2 (1mg, 0.004mmol), p-toluenesulfonyl azide (79mg, 0.40mmol), phenol (8mg, 0.08mmol), acetonitrile 4ml, the system was evacuated to 20mmHg, then filled with CO gas to normal pressure, and so repeated for 3 Second-rate. After the system was vigorously stirred at room temperature for 6 hours, 2-amino-4-methoxy-6-methyl-1,3,5-triazine (67mg, 0.48mmol) was added, and the system was placed at 80°C The reaction was stirred under an oil bath for 20 h, the solvent was concentrated under reduced pressure, and the residue was separated and purified by column chromatography (dichloromethane: met...

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Abstract

The invention relates to a preparation method of a compound represented by a formula (I). The compound is prepared by reacting a compound represented by a formula (II) with a compound represented by a formula (III) in a solvent under the catalysis of a palladium catalyst in carbon monoxide atmosphere, wherein X is O or N; N is 0 or 1; when X is O, n is equal to 0; when X is N, n is equal to 1; R1 is selected from aryl, heteroaryl, alkyl, alkenyl or alkynyl; R2 is selected from aryl, heteroaryl, alkyl, alkenyl or alkynyl; R3 is selected from H, R2 forms a ring, or R2 and R2 are linked to form a ring; R4 is N3 or a halogen atom; when R4 is the halogen atom, a system further contains sodium azide. The preparation method has the beneficial effects that the reaction does not require strict anhydrous and anaerobic conditions and high-pressure carbon monoxide atmosphere, the operation is convenient and simple, and the reaction has very good tolerance and universality to functional groups; meanwhile, the use level of a catalyst is extremely low, the reaction cost is very low, and the method can be widely applied to the preparation of sulfonylurea compounds.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of sulfonylureas and sulfonamido formate compounds. Background technique [0002] Sulfonylureas and sulfonamidocarbamate compounds are a very important class of organic compounds, which are widely used in the fields of medicine, pesticides and polymer functional materials. For example, in the field of medicine, sulfonylurea compounds can be effectively used in the treatment of type II diabetes, they bind the K on the membrane of pancreatic cells ATP channel, inhibiting the outflow of potassium ions, thereby increasing the release of insulin. Another example is in the field of pesticides, sulfonylurea compounds are an important class of herbicides, which selectively inhibit acetolactate synthase (ALS) / acetate hydroxyacid synthase (AHAS), low toxicity, high efficiency and high selectivity. [0003] For a long time, people have been looking for sim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/58C07C311/60C07C303/36C07F5/02C07D295/215C07D239/52C07C311/53C07C311/55C07D333/34C07D251/16
Inventor 张振华赵晋李宗洋傅滨王明安
Owner CHINA AGRI UNIV
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