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Synthetic method of 2-amino-4-(ethylsulfonyl) phenol

A technology of ethylsulfonyl and synthesis method, which is applied in the field of synthesis of 2-amino-4-phenol, can solve the problems of poor product quality, harsh reaction process, and high production cost

Active Publication Date: 2016-05-11
苏州正济药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, no matter from the theoretical and experimental verification results of organic chemistry, the existing preparation route has obvious defects, harsh reaction process, poor safety, high production cost, and poor product quality.

Method used

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  • Synthetic method of 2-amino-4-(ethylsulfonyl) phenol
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  • Synthetic method of 2-amino-4-(ethylsulfonyl) phenol

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preparation example Construction

[0036] The invention provides a kind of synthetic method of 2-amino-4-(ethylsulfonyl)phenol, comprising the following steps:

[0037] a) After reacting 4-ethanesulfonyl-2-nitro-chlorobenzene with a base in a solvent, 4-(ethylsulfonyl)-2-nitro-phenol is obtained;

[0038] b) Reducing the 4-(ethylsulfonyl)-2-nitro-phenol obtained in the above steps to obtain 2-amino-4-(ethylsulfonyl)phenol.

[0039] In the present invention, 4-(ethylsulfonyl)-2-nitro-chlorobenzene is reacted with a base in a solvent to obtain 4-(ethylsulfonyl)-2-nitro-phenol.

[0040] The present invention is not particularly limited to the 4-ethanesulfonyl-2-nitro-chlorobenzene, 4-ethanesulfonyl-2-nitro-chlorobenzene well-known to those skilled in the art can be used, and the 4-nitro-chlorobenzene described in the present invention -Ethyl-2-nitro-chlorobenzene preferably has the structure of formula IV,

[0041]

[0042] The present invention is not particularly limited to the 4-(ethanesulfonyl)-2-nitro-ph...

Embodiment 1

[0081] 4-Ethylsulfonyl-chlorobenzene

[0082] Into a 2L glass reaction bottle, sequentially add 100g of 4-chlorophenethyl sulfide, 1.0g of sodium tungstate dihydrate and 300mL of ethyl acetate; at 40°C, start to add 35% H 2 o 2 190g, control the temperature at 40-50°C, keep warm for half an hour after dripping, then raise the temperature to 55°C, and react for 3 hours; TLC monitors that the reaction is complete, cool down to 20-30°C, add saturated Na 2 SO 3 solution until the potassium iodide test paper does not change color. Stir evenly, stand to separate the organic layer, extract the aqueous layer with 400ml ethyl acetate, combine the organic layers, wash with 300ml brine, dry over anhydrous sodium sulfate, and concentrate to obtain 125g colorless oily 2-nitro-4-ethanesulfonate The crude product of acyl chloride benzene was directly used in the next reaction.

[0083] 4-Ethylsulfonyl-2-nitro-chlorobenzene

[0084] To a 1L glass reaction bottle, add 100g of crude 2-nitr...

Embodiment 2

[0100] 4-Ethylsulfonyl-chlorobenzene

[0101] Into a 250ml glass reaction bottle, sequentially add 20g of 4-chlorophenethyl sulfide, 0.2g of sodium tungstate dihydrate and 60mL of acetic acid; at 40°C, start to drop 40g of 35% H 2 o 2 , control the temperature at 40-50°C, after dropping, keep warm for half an hour, then raise the temperature to 55°C, and react for 3 hours; TLC monitors that the reaction is complete, cool down to 20-30°C, add saturated Na 2 SO 3 solution until the potassium iodide test paper does not change color. Extracted 3 times with 100ml ethyl acetate, combined the organic layers, washed 3 times with 100ml brine, dried over anhydrous sodium sulfate, concentrated to obtain about 25g colorless oily 2-nitro-4-ethanesulfonylchlorobenzene crude product, directly used react in the next step.

[0102] 4-Ethylsulfonyl-2-nitro-chlorobenzene

[0103] Add 25g of crude 4-ethanesulfonyl-chlorobenzene and 75ml of glacial acetic acid to a 250ml glass reaction bottle, ...

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Abstract

The invention provides a synthetic method of 2-amino-4-(ethylsulfonyl) phenol. The method comprises the following steps that firstly, 4-ethylsulfonyl-2-nitro-chlorobenzene and alkali are subjected to a reaction in a solvent to obtain 4-(ethylsulfonyl)-2-nitro-phenol; then, the 4-(ethylsulfonyl)-2-nitro-phenol obtained in the last step is reduced to obtain 2-amino-4-(ethylsulfonyl) phenol. The novel synthesis route is designed, no high temperature or high pressure is needed in the reaction process, reaction conditions are mild, and the reaction yield and product purity are high, so that the production cost of the product is lowered, the product quality is improved, the preparation technology is more reasonable, and large batch industrial production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2-amino-4-(ethylsulfonyl)phenol. Background technique [0002] 2-amino-4-(ethylsulfonyl)phenol, also known as 2-amino-4-(ethylsulfonyl)phenol, 2-amino-4-ethylsulfonylphenol, English name 2-Amino-4-( ethylsulfonyl)phenol, molecular weight 201.24, CAS#:43115-40-8, molecular formula H 2 NC 6 h 3 (SO 2 C 2 h 5 )OH, with the structure shown in formula I, [0003] [0004] 2-Amino-4-(ethylsulfonyl)phenol is an important chemical intermediate widely used in dyes, medicines, pesticides, rubber additives, photosensitive materials and other fields. In the field of medicine, this product is mainly used in the synthesis of new drugs such as anti-inflammatory and analgesic drugs, antibiotics and poly(ADP-ribose) polymerase (PARP) inhibitors. [0005] However, at present, there is only one Japanese patent JPH01149762A report about the synt...

Claims

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Application Information

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IPC IPC(8): C07C317/36C07C315/04
CPCC07C315/04C07C317/36C07C317/22
Inventor 孟祥云袁果李恂李朋孙光福
Owner 苏州正济药业有限公司
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