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Synthesis method of thermosensitive sensitizer N-p-tolylsulfonyl-N'-(3-p-tolylsulfonyl oxyphenyl) urea

A technology of toluenesulfonyloxyphenyl and p-toluenesulfonyl, which is applied in the field of synthesis of heat-sensitive sensitizers, can solve the problems of low total yield, and achieve the effects of simple operation, suitability for industrial production, and high yield

Active Publication Date: 2017-11-03
WEIFANG DAYOU BIOLOGICAL CHEM CO LTD
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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 method with milder reaction conditions, easier operation, higher yield and more suitable for industrial production in view of the cumbersome steps of two-step post-treatment in the aforementioned patents and the disadvantages of low overall yield. Synthesis method of thermosensitive sensitizer N-p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea

Method used

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  • Synthesis method of thermosensitive sensitizer N-p-tolylsulfonyl-N'-(3-p-tolylsulfonyl oxyphenyl) urea
  • Synthesis method of thermosensitive sensitizer N-p-tolylsulfonyl-N'-(3-p-tolylsulfonyl oxyphenyl) urea

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Experimental program
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Embodiment 1

[0024] Add m-aminophenol (10.3g, 0.0945mol) and p-toluenesulfonyl isocyanate (20.45g, 0.104mol) to acetonitrile (90mL) successively, stir at room temperature overnight, then add 50mL of water and (10.7g, 0.126mol) 47% Sodium hydroxide aqueous solution, then add p-toluenesulfonyl chloride (19.86g, 0.104mol), after addition, react at 40°C for 2 hours, cool down to room temperature, neutralize with hydrochloric acid to precipitate a white solid, filter, wash with water, and dry to obtain 42.6g of white solid N-p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea, the yield is 98%, and the melting point is 156-159°C.

[0025] The characterization result of product N-toluenesulfonyl-N'-(3-toluenesulfonyloxyphenyl) urea is as follows:

[0026] 1 H NMR (500MHz, DMSO-d 6 )δ=10.81(s,1H),9.13(s,1H),7.82-7.84(d,2H),7.70-7.71(d,2H),7.42-7.44(d,4H),7.17-7.25(m, 3H), 6.57-6.59(d, 1H), 2.40(s, 6H) ppm.ESI-MS: (m / z, %)=461[M+H] + .

Embodiment 2

[0028] Add m-aminophenol (9.32g, 0.0855mol) and p-toluenesulfonyl isocyanate (20.45g, 0.104mol) to acetonitrile (100mL) successively, stir at 40°C for 4h, then add 50mL of water and (15.7g, 0.196mol) 50% sodium hydroxide aqueous solution, then add p-toluenesulfonyl chloride (15.89g, 0.0832mol), after addition, react at 60°C for 4.5 hours, cool down to room temperature, neutralize with hydrochloric acid to precipitate a white solid, filter, wash with water, and dry to obtain a white solid N-p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea, the yield is 97%, and the melting point is 155-158°C.

Embodiment 3

[0030] Add m-aminophenol (13.60g, 0.125mol) and p-toluenesulfonyl isocyanate (20.45g, 0.104mol) to acetonitrile (150mL) successively, stir at room temperature overnight, then add 50mL of water and (12.19g, 0.0914mol) 30% Sodium hydroxide aqueous solution, then add p-toluenesulfonyl chloride (23.30g, 0.122mol), after addition, react at 90°C for 1 hour, cool down to room temperature, neutralize with hydrochloric acid to precipitate a white solid, filter, wash with water, and dry to obtain a white solid N- p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea, the yield is 98%, and the melting point is 154-158°C.

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Abstract

The invention provides a synthesis method of a thermosensitive sensitizer N-p-tolylsulfonyl-N'-(3-p-tolylsulfonyl oxyphenyl) urea. The m-aminophenol and the p-toluenesulfonyl isocyanate firstly react to generate N-[(3-hydroxy phenyl) formamyl]-4-toluenesulfonamide, the paratoluensulfonyl chloride is directly reacted with the above mixture without processing the reaction so as to obtain the N-p-tolylsulfonyl-N'-(3-p-tolylsulfonyl oxyphenyl) urea, and the product yield is up to more than 98%.

Description

technical field [0001] The invention belongs to the synthetic field of thermosensitive sensitizers, in particular to a synthetic method of thermosensitive sensitizer N-p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea. Background technique [0002] The compound N-p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea is a new type of heat-sensitive sensitizer for heat-sensitive recording paper. In addition to sensitivity, it also endows the recorded image with high optical density and clarity, which can improve the sensitivity, thermal stability, sensitivity, luminosity and other properties of thermal recording paper. [0003] World patent WO2000035679 and Japanese patent JP2010131763 disclose a thermosensitive recording material, and disclose the preparation method of N-p-toluenesulfonyl-N'-(3-p-toluenesulfonyloxyphenyl) urea, both of which are First react with m-aminophenol and p-toluenesulfonyl chloride, separate and obtain 3-aminophenyl 4-methylbenzenesulfonate...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/60
CPCC07C303/40C07C311/60
Inventor 耿潇李峰宋艳宋晓峰
Owner WEIFANG DAYOU BIOLOGICAL CHEM CO LTD
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