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Process for synthesizing 1- methylamino-1-methoxy-2-nitroethylene

A technology of nitroethylene and a synthesis method, applied in the field of compounds, can solve the problems of complicated operation, long reaction time, expensive trimethyloxonium tetrafluoroborate, etc., and achieves improved operation safety, reduced labor intensity, and shortened production. effect of cycles

Active Publication Date: 2012-04-25
福建深纳生物工程有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of this synthetic method is: (a) reaction process needs to carry out in dichloromethane solvent, and its operation and discharge are extremely unfriendly to environment; (b) used reagent trimethyloxonium tetrafluoroborate is comparatively expensive; ( c) complex operation, longer reaction time, not suitable for industrial production; (d) low reaction yield and high cost

Method used

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  • Process for synthesizing 1- methylamino-1-methoxy-2-nitroethylene
  • Process for synthesizing 1- methylamino-1-methoxy-2-nitroethylene
  • Process for synthesizing 1- methylamino-1-methoxy-2-nitroethylene

Examples

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Effect test

Embodiment 1

[0021] Add 500ml of anhydrous methanol to a 1000ml three-necked round-bottomed flask with a magnetic stirrer, reflux condenser and thermometer, add 2.3g (0.1mol) of sodium metal under stirring, and then add 149g (1mol) after the sodium metal is dissolved. 1-Methylamino-1-methylthio-2-nitroethylene, stir and heat up to 60°C, react for 2-5 hours, evaporate methanol to dryness under reduced pressure to obtain a yellow solid, directly add 1500ml of absolute ethanol and heat up to reflux for 1h, Cool to below room temperature, filter, and wash the filter cake once with absolute ethanol to obtain 80.5 g of 1-methylamino-1-methoxy-2-nitroethylene as a light yellow solid, with a yield of 61% and a purity of 98.5% .

Embodiment 2

[0023] Add 500ml of anhydrous methanol to a 1000ml three-necked round-bottom flask with a magnetic stirrer, reflux condenser and thermometer, add 4g of metal potassium under stirring, and then add 149g of 1-methylamino-1-methylsulfide after the metal sodium is dissolved Base-2-nitroethylene, stir and heat up to 60°C, react for 2-5h, evaporate methanol to dryness under reduced pressure to obtain a yellow solid, directly add 1500ml of absolute ethanol, heat up to reflux for 1h, cool to below room temperature, filter, filter cake Wash once with absolute ethanol to obtain 1-methylamino-1-methoxy-2-nitroethylene as a light yellow solid.

Embodiment 3

[0025] Add 4500ml of anhydrous methanol to a 5000ml four-necked round bottom flask with a magnetic stirrer, reflux condenser and thermometer, add 56.7g (0.15mol) of sodium methoxide under stirring, and then add 1043g (7mol) after the sodium methoxide is dissolved. 1-Methylamino-1-methylthio-2-nitroethylene, stir and heat up to reflux, react for 2-5 hours, evaporate methanol to dryness under reduced pressure to obtain a yellow solid, directly add 1500ml of absolute ethanol, heat up to reflux for 1h, cool After cooling down to room temperature, filter and wash the filter cake once with absolute ethanol to obtain 600.5 g of 1-methylamino-1-methoxy-2-nitroethylene as a light yellow solid with a yield of 65%.

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Abstract

A method for synthesizing 1-methyl amino-1-methoxy-2-nitroethylene relates to a compound. The invention provides a method of high yield coefficient and purity quotient for synthesizing 1-methyl amino-1-methoxy-2-nitroethylene, the method is applicable to large-scale industrial production. A catalyst is dissolved in absolute methanol solution; 1-methyl amino-1-methyl mercapto-2-nitroethylene are added in, stirred and heated up to reflow; the methyl alcohol is processed by reduced pressure evaporation to dryness to obtain a yellow solid matter; and the solid matter obtained by recrystalization by ethyl alcohol is the target product. The invention does not need to use methylene dichloride highly toxic solvent, thereby having advantages in production operation safety and environmental protection. The used raw materials are low in cost and available, unit operations are less, the steps like extraction and dryness, and the like, are saved, the operation safety of operating personnel is improved, the unit operation production period is shortened, and the production cost is greatly reduced, thus being suitable for industrial production. The yield coefficient of the reaction can be increased from 35.2% to 40-65%, thus obviously reducing the cost.

Description

technical field [0001] The invention relates to a compound, in particular to a synthesis method of 1-methylamino-1-methoxy-2-nitroethylene, one of the main intermediates of ranitidine, a drug for peptic ulcer. Background technique [0002] The molecular structural formula of 1-methylamino-1-methoxy-2-nitroethene (1-methoxy-N-methyl-2-nitroethenamine) is: [0003] [0004] 1-methylamino-1-methoxy-2-nitroethylene (referred to as compound (I)) is one of the main intermediates of ranitidine, a peptic ulcer drug, and its production directly affects ranitidine The cost of titin. European Patent 230127 A1 firstly described the method for synthesizing compound (I), and its specific steps are as follows: [0005] First add N-methyl-2-nitroacetamide, use dichloromethane as solvent, then add trimethyloxonium tetrafluoroborate, stir and react at 25°C for about 20h, add saturated sodium carbonate solution, let stand The organic layer was separated, the aqueous layer was extracted w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/26C07C213/00
Inventor 马增欣朱少龙游金龙崔朋娟王亚璐
Owner 福建深纳生物工程有限公司
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