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3-amido-4-alkylamino lauseto neu preparation method

A technology of alkylaminophenylmethyl sulfone and nitrophenylmethyl sulfone, which is applied in the field of preparation of 3-amino-4-alkylaminophenylmethyl sulfone, which can solve the problems of raw material sources, low reduction yield, environmental pollution, etc. problems, to achieve the effect of mild conditions, high purity, and less waste

Inactive Publication Date: 2006-07-12
杭州神鹰制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The main preparation method of existing 3-amino-4-alkylaminophenylmethyl sulfone is to use sodium dithionite to reduce 4-methylamino 3-nitrophenylmethylsulfone into 3-amino-4-alkylaminophenylmethylsulfon

Method used

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  • 3-amido-4-alkylamino lauseto neu preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The first step of synthesis of sodium p-chlorobenzenesulfinate

[0017] Add 144g (1.14mol) of anhydrous sodium sulfite, 820ml of water, 240g (2.86mol) of anhydrous sodium bicarbonate into a 2000ml four-neck flask, heat the oil bath to 70°C, add 233.6g (1.11mol) of p-chlorobenzenesulfonyl chloride, Keep warm at 70-80°C, stir for 2.5 hours, cool down to room temperature, and use it directly for the next reaction.

[0018] Synthesis of p-chlorophenylmethyl sulfone in the second step

[0019] Add 127.5 g (1.3 mol) of chloroacetic acid and 18 g of p-toluenesulfonic acid to the reaction liquid in the previous step, heat up the oil bath to 105° C., and reflux for 8 hours until no bubbles bubble out in the reaction liquid. Cool in a water bath, filter with suction, wash with water three times, and dry to obtain 193.2 g of p-chlorophenylmethyl sulfone as a white granular solid, mp: 95-96°C, yield 91.6%.

[0020] The third step of synthesis of 4-chloro-3-nitrophenyl methyl sulf...

Embodiment 2

[0027] The first step of synthesis of sodium p-chlorobenzenesulfinate

[0028] Add 181.7g (1.15mol) of anhydrous potassium sulfite, 820ml of water, 300g (3.0mol) of anhydrous potassium bicarbonate into a 2000ml four-neck flask, heat up the oil bath to 70°C, add 233.6g (1.11mol) of p-chlorobenzenesulfonyl chloride mol), kept at 70-80°C, stirred and reacted for 2 hours, cooled down to room temperature, and used directly for the next reaction.

[0029] Synthesis of p-chlorophenylmethyl sulfone in the second step

[0030] 154.3 g (1.11 mol) of bromoacetic acid and 18 g of p-toluenesulfonic acid were added to the reaction solution in the previous step, and the oil bath was heated to 90° C., and the rest was the same as in the second step of Example 1 to obtain white granular solid p-chlorophenylsulfone.

[0031] The third step of synthesis of 4-chloro-3-nitrophenyl methyl sulfone

[0032] Slowly add 40.5ml (74.5g) of concentrated sulfuric acid to 192.2ml (296g) of fuming nitric a...

Embodiment 3

[0038] The first step of synthesis of sodium p-chlorobenzenesulfinate

[0039] Add 153.8g (1.22mol) of anhydrous sodium sulfite, 850ml of water, 186.5g (2.22mol) of anhydrous sodium bicarbonate into a 2000ml four-neck flask, heat the oil bath to 70°C, add 233.6g (1.11mol) of p-chlorobenzenesulfonyl chloride ), kept at 85-90°C, stirred and reacted for 3 hours, cooled down to room temperature, and used directly for the next reaction.

[0040] Synthesis of p-chlorophenylmethyl sulfone in the second step

[0041] Add 131.1 g (1.39 mol) of chloroacetic acid and 20 g of methanesulfonic acid to the reaction solution in the previous step, and heat up the oil bath to reflux. The rest is the same as the second step of Example 1 to obtain white granular solid p-chlorophenylmethyl sulfone.

[0042] The third step of synthesis of 4-chloro-3-nitrophenyl methyl sulfone

[0043]Slowly add 64.5ml (118.7g) of concentrated sulfuric acid to 163.4ml (251.6g) of fuming nitric acid to prepare a mi...

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Abstract

The invention discloses a method for preparing for 3-amido -4-alkylamino radical lauseto neu, which comprises the following steps: first using toluene sulfochloride as raw material and using sulfurous acid to convert it into chlorobenzene sulfonate, using alkylsulfonic acid as catalyst to do compression decarboxylation reaction to the halogenated acetic acids to generate chlorobenzene sulfonate, then itrating in the mixed acid to prepare for the 4-chloro-3-nitro lauseto neu; then using alkyl replacement amine to do nucleophilic substitution in alcohol to prepare for 4-alkylamino radical -3-nitro lauseto neu, at last using redactor to redact the nitro into 3-amido -4-alkylamino radical lauseto neu.

Description

technical field [0001] The invention relates to a preparation method for synthesizing fluorescent whitening agent intermediate compound 3-amino-4-alkylaminophenylmethyl sulfone. Background technique [0002] The main preparation method of existing 3-amino-4-alkylaminophenylmethyl sulfone is to use sodium dithionite to reduce 4-methylamino 3-nitrophenylmethylsulfone into 3-amino-4-alkylaminophenylmethylsulfone (Dyes and Pigments (1989), 11 (2), 147-161), the shortcoming of this method is that reduction yield is low, only has 52%, and by-product is more, pollutes environment, and raw material source is difficult. Contents of the invention [0003] The purpose of the present invention is to provide a method for preparing 3-amino-4-alkylaminophenylmethyl sulfones with less waste, high yield, low cost and stable product quality. [0004] The preparation method of 3-amino-4-alkylaminophenylmethyl sulfone of the present invention comprises the steps successively: [0005] The f...

Claims

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Application Information

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IPC IPC(8): C07C317/36C07C315/00
Inventor 戴立言姜昕鹏
Owner 杭州神鹰制药有限公司
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