6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione and its preparation method

A technology of dichloromethane and compounds, applied in the field of 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione and its preparation, can solve unfavorable industrialization Production, expensive, troublesome operation and other issues

Active Publication Date: 2015-08-19
CHANGZHOU NO 4 PHARMA FACTORY +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is cumbersome to operate, and triphenyl borate needs to be added as a reaction aid, which is expensive and unfavorable for industrial production

Method used

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  • 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione and its preparation method
  • 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione and its preparation method
  • 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Synthesis of 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione

[0017] Dissolve 19.0 g of triphosgene in 90 ml of CH 2 Cl 2 Placed in a four-necked bottle, N 2 Under air flow, 2-hydroxy-4,5-dimethoxybenzoic acid (22.2 g) was dissolved in 150 ml CH 2 Cl 2 and 45ml of pyridine, drop it into a four-neck flask under an ice-salt bath and control the temperature at 0-5°C. The dropwise addition was completed within 45 minutes, and kept stirring at low temperature for 10 minutes. Then rise to room temperature (20° C.) and stir for 50 min to stop the reaction. Suction filtration under normal pressure, and the filtrate was rotary evaporated at room temperature to constant weight to obtain the product, which was directly used in the next reaction without purification. M+H 225.

Embodiment 2

[0019] Synthesis of 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione

[0020] Dissolve 9.0 g of triphosgene in 40 ml of CH 2 Cl 2 Placed in a four-necked bottle, N 2 Under air flow, 2-hydroxy-4,5-dimethoxybenzoic acid (10.2 g) was dissolved in 75 ml CH 2 Cl 2 and 20ml of pyridine were dropped into a four-neck flask under an ice-salt bath to control the temperature at 5°C. After the dropwise addition, keep stirring at low temperature for 10 min. Then it was raised to room temperature (20° C.) and stirred for 1 h to stop the reaction. Suction filtration under normal pressure, and the filtrate was rotary evaporated at room temperature to constant weight to obtain the product.

Embodiment 3

[0022] Synthesis of 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione

[0023] Dissolve 27.0 g of triphosgene in 100 ml of CH 2 Cl 2 Placed in a four-necked bottle, N 2 Under air flow, 2-hydroxy-4,5-dimethoxybenzoic acid (30.6 g) was dissolved in 200 ml CH 2 Cl 2 and 40ml of pyridine were dropped into a four-neck flask under an ice-salt bath to control the temperature at 0°C. After the dropwise addition, keep stirring at low temperature for 10 min. Then it was raised to room temperature (20° C.) and stirred for 1 h to stop the reaction. Suction filtration under normal pressure, and the filtrate was rotary evaporated at room temperature to constant weight to obtain the product.

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Abstract

The invention discloses a compound of formula (1) and a preparation method thereof. The compound of the formula (1) is used for preparing the intermediate of acotiamide hydrochloride (Z-338).

Description

technical field [0001] The present invention relates to 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione and its preparation method. The 6,7-dimethoxy-benzo[d][1,3]dioxene-2,4-dione is an intermediate for the preparation of acotiamide hydrochloride (Z-338). Background technique [0002] Acotiamide hydrochloride (Z-338) is a new type of M1 and M2 receptor antagonist originally developed by Zeria Company in Japan, which is clinically used to treat functional dyspepsia. Its compound patent application (CN96194002.6) chooses to use 2,4,5-trimethoxybenzoic acid as a raw material to react with ethyl 2-aminothiazole-4-formate to generate 2-[(2-hydroxyl-4,5- Dimethoxybenzoyl) amino]-1,3-thiazole-4-carboxylic acid ethyl ester, and then remove the 2-position methyl group of the benzene ring, the yield of this method is low, and the demethylation selectivity is not good. Therefore, it is better to choose to remove the methyl group at the 2-position first, and then carry out the subsequen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/08C07D277/56
Inventor 谢智乾王哲烽益兵刘启皓钟静芬时惠麟王晓东潘璐申聪云黄素萍时敏
Owner CHANGZHOU NO 4 PHARMA FACTORY
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