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N-acyl phenothiazine and preparation method thereof

A technology of acyl phenothiazine and phenothiazine, which is applied in the field of N-acyl phenothiazine and its preparation, can solve the problems of long reaction process time, troublesome post-processing, environmental pollution and the like, and achieves short reaction time and little environmental pollution. , post-processing simple effects

Inactive Publication Date: 2014-10-22
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction process takes a long time, and many organic solvents are used in the reaction process, which causes serious environmental pollution and troublesome post-processing

Method used

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  • N-acyl phenothiazine and preparation method thereof
  • N-acyl phenothiazine and preparation method thereof
  • N-acyl phenothiazine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 0.0055mol benzoic acid and 0.0055mol phosphorus pentachloride to a dry mortar, grind for 0.5h at room temperature until the grinding is uniform, then add 0.005mol phenothiazine, continue grinding, monitor the reaction with TLC, until the phenothiazine is completely reacted At this time, the raw material point of phenothiazine disappeared, and the grinding was stopped to obtain the product, wherein the developer used for TLC monitoring was a mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:3, and then the product was allowed to stand at room temperature for 1h ; Then wash with suction and filter, dry the filter cake at room temperature for 24 hours and then recrystallize with water to obtain N-acylphenylphenothiazine. The yield was 92.4%. The melting point is 150-154°C.

[0031] IR(KBr,cm -1 ):3089cm -1 ,3056cm -1 (Unsaturated C-H); 1671cm -1 (amide); 1596cm -1 , 1502cm -1 , 1472cm -1 (benzene ring vibration absorption peak); 1256c...

Embodiment 2

[0033] Add 0.0055mol m-toluic acid and 0.0055mol phosphorus pentachloride to a dry mortar, grind for 1 hour at room temperature until the grinding is uniform, then add 0.005mol phenothiazine, continue grinding, monitor the reaction with TLC, until the phenothiazine Reaction is complete, and now the raw material point of phenothiazine disappears, and the grinding is stopped to obtain the product, wherein the developing agent used for TLC monitoring is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3, and then the product is statically placed at room temperature. Set aside for 0.5h; then wash with water and filter with suction, dry the filter cake at room temperature for 22h and then recrystallize with water to obtain N-acyl m-methylphenylphenothiazine. The yield was 94.8%. The melting point is 110-112°C.

[0034] IR(KBr,cm -1 ):3098cm -1 ,3054cm -1 (Unsaturated C-H); 2994cm -1 ,2911cm -1 (saturated C-H); 1656cm -1 (amide); 1595cm -1 , 1500cm...

Embodiment 3

[0036] Add 0.005mol p-chlorobenzoic acid and 0.0055mol phosphorus pentachloride to a dry mortar, grind for 0.8h at room temperature until the grinding is uniform, then add 0.005mol phenothiazine, continue grinding, monitor the reaction with TLC, until the phenothiazine Reaction is complete, and now the raw material point of phenothiazine disappears, and the grinding is stopped to obtain the product, wherein the developing agent used for TLC monitoring is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3, and then the product is statically placed at room temperature. Set aside for 0.8h; then wash with water and filter with suction, dry the filter cake at room temperature for 23h and then recrystallize with water to obtain N-acyl p-chlorophenylphenothiazine. The yield was 93.6%. The melting point is 134-139°C.

[0037] IR(KBr,cm -1 ):3089cm -1 , 3024cm -1 (Unsaturated C-H); 1654cm -1 (amide); 1598cm -1 , 1502cm -1 , 1459cm -1 (benzene ring vib...

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Abstract

The invention relates to N-acyl phenothiazine and a preparation method thereof. A structural formula of N-acyl phenothiazine is shown as the formula (I). The formula (I) is shown in the description. The preparation method of N-acyl phenothiazine comprises the steps of adding A mol of an aromatic acid and B mol of phosphorus pentachloride in a reaction vessel; grinding uniformly; then adding C mol of phenothiazine; grinding continuously until phenothiazine is reacted completely to obtain a product; standing the product; washing the product with water; carrying out suction filtration; drying a filter cake; and carrying out recrystallization to obtain N-acyl phenothiazine. A ratio of A to B to C is (1-1.2):(1-1.2):1. A solid phase synthetic method is adopted; and reactants are directly grounded for reaction. The preparation method is mild in conditions, short in reaction time, obvious in reaction phenomena, simple and convenient for operations, and low in equipment requirement. A catalyst of phosphorus pentachloride is cheap, and has small toxicity and small pollution to environment. The yield of a target product can reach over 92%. The preparation method is a simple, convenient, environment-friendly and safe method for preparing N-acyl phenothiazine.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to an N-acyl phenothiazine and a preparation method thereof. Background technique [0002] Phenothiazine is an aromatic heterocyclic compound containing nitrogen and sulfur atoms. It is an electron-rich group with a large π-conjugated system in the molecule. It has a low oxidation potential and is easy to form stable free radical cations. The delocalization of electrons makes the whole molecule more rigid and planar, and has strong fluorescence characteristics and structural regulation. Therefore, these characteristics make phenothiazine and its derivatives have unique application prospects in NLO, electron transfer, energy exchange, photoreduction, molecular labeling, drug catalysis, and nano-modification. In the 1850s, phenothiazine drugs were used as tranquilizers and stabilizers. It was also reported that phenothiazine can be used to inhibit certain infectious dise...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/30C07D417/06
CPCC07D279/30C07D417/06
Inventor 刘玉婷刘蓓蓓尹大伟靖春燕张晓莉杨阿宁宋思梦王金玉
Owner SHAANXI UNIV OF SCI & TECH
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