Synthetic method of deuterium-marked sulfanilamide

Active Publication Date: 2012-07-25
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a simple and efficient one-step synthesis method of deuterium-labeled sulfonamide in order to overcome the defects in the above-mentioned prior art, and solve the technical problems of expensive raw materials, complicated operation and low yield in the prior art

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  • Synthetic method of deuterium-marked sulfanilamide
  • Synthetic method of deuterium-marked sulfanilamide
  • Synthetic method of deuterium-marked sulfanilamide

Examples

Experimental program
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Effect test

Embodiment 1

[0028] R 1 =i, sulfadiazine-benzene ring-D 4 Synthesis

[0029] acetaminobenzenesulfonic acid-benzene ring-D 4 (2.192g, 10mmol), N-chlorosuccinimide (1.600g, 12mmol), and acetone (50ml) were placed in a reaction flask, and stirred at 15-20°C for 0.5h. The mixture was cooled to 0-5°C with an ice-water bath, palladium (0.200g) was added to the reactant, and an acetone solution containing pyridine (1.58g, 20mol) and 2-aminopyrimidine (i) (1.045g, 11mmol) was added dropwise 5ml, after the dropwise addition, stir and react at 20-25°C for 2h. After the reaction, filter, add 10ml of water to the filtrate, neutralize the pH to 5-6 with 1N hydrochloric acid, wash twice with 50ml of water, dry with a desiccant, filter, and concentrate the filtrate to dryness under reduced pressure. Put the obtained solid in a reaction bottle, add 5ml of 30% sodium hydroxide, react at 60°C for 15min, cool the reaction system to 0-5°C in an ice-water bath, add 1N hydrochloric acid to neutralize the pH...

Embodiment 2

[0031] R 1 =ii, sulfamethazine-benzene ring-D 4 Synthesis

[0032]P-acetaminobenzenesulfonic acid (2.192g, 10mmol), N-chlorosuccinimide (1.600g, 12mmol), and acetone (50ml) were placed in a reaction flask, and stirred at 20-25°C for 1h. The mixture was cooled to 0-5°C with an ice-water bath, iridium (0.200g) was added to the reactant, and a mixture containing pyridine (1.580g, 20mol), 2-amino-4,6-dimethylpyrimidine (ii) was added dropwise ( 1.353g, 11mmol) of acetone solution in 5ml, after the dropwise addition was completed, the reaction was stirred at 20-25°C for 2.5h. After the reaction, filter, add 10ml of water to the filtrate, neutralize the pH to 5-6 with 1N hydrochloric acid, wash twice with 50ml of water, dry with a desiccant, filter, and concentrate the filtrate to dryness under reduced pressure. Put the obtained solid in a reaction flask, add 5ml of 30% sodium hydroxide, react at 60°C for 15 minutes, cool the reaction system to 0-5°C in an ice-water bath, add 1N ...

Embodiment 3

[0034] R 1 =iii, sulfamethoxine-benzene ring-D 4 Synthesis

[0035] acetaminobenzenesulfonic acid-benzene ring-D 4 (2.192g, 10mmol), N-chlorosuccinimide (1.600g, 12mmol), and acetone (50ml) were placed in a reaction flask, and stirred at 10-15°C for 1h. Cool the mixture to 0-5°C with an ice-water bath, add indium (0.100g) to the reactant, and dropwise add pyridine (1.580g, 20mol), 2-amino-5-methoxypyrimidine (iii) (1.375g , 11mmol) of acetone solution in 5ml, after the dropwise addition was completed, the reaction was stirred at 20-25°C for 2h. After the reaction, filter, add 10ml of water to the filtrate, neutralize the pH to 5-6 with 1N hydrochloric acid, wash twice with 50ml of water, dry with a desiccant, filter, and concentrate the filtrate to dryness under reduced pressure. Put the obtained solid in a reaction flask, add 5ml of 30% sodium hydroxide, react at 60°C for 20 minutes, cool the reaction system to 0-5°C in an ice-water bath, add 1N hydrochloric acid to neutr...

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Abstract

The invention relates to a synthetic method of deuterium-marked sulfanilamide. The method comprises the following steps of: reacting deuterated sulfonic acid with N-chlorosuccinimide (NCS) to obtain deuterated sulfonyl chloride which is not required to be separated; and adding amine for undergoing an amination reaction under the action of a metal catalyst to obtain deuterium-marked sulfanilamide. Compared with the prior art, the method has the advantages that: acyl chloride synthesis and the amination reaction are performed with a 'one pot process', operation is simple and convenient, the yield is high, and a synthesized product comprises sulfapyridine-benzene ring-D4, sulfadimidine-benzene ring-D4, sulfameter-benzene ring-D4, sulfaquinoxaline-benzene ring-D4, sulfisoxazole-benzene ring-D4 and sulfamethoxazole-benzene ring-D4.

Description

technical field [0001] The invention relates to the field of deuterium-labeled compounds, in particular to a method for synthesizing deuterium-labeled sulfonamides. Background technique [0002] Sulfonamides are broad-spectrum antibiotics with a long metabolic cycle and are likely to remain in fish, meat and eggs. Due to the large amount of sulfonamides used in the aquaculture industry, very serious food safety problems have occurred. Deuterium-labeled sulfonamide is mainly used as an internal standard reagent for the detection of sulfonamide residues in fish, meat and eggs. [0003] The organic synthesis of deuterium-labeled sulfaline has not been reported, and there are many methods for natural abundance sulfaline so far. As early as 1944, John Weijlard et al. (Weijlard J, TishlerM, EricksonE, Sulfaquioxaline and some related compounds[J], Journal of the American Chemical Society, 1954, 66 (11): 1957~1959) et al. synthesized sulfaquinoxaline for the first time by reactin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/69C07D241/44C07D261/14
Inventor 卢伟京费荣杰李帅杜晓宁徐仲杰卢浩
Owner SHANGHAI RES INST OF CHEM IND
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