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Method for preparing ethylmethylamino formyl chloride

A technology of ethyl methyl carbamoyl and ethyl formamide is applied in the field of preparation of ethyl methyl carbamoyl chloride, can solve problems such as excessive length, and achieve the effects of short route, reduction of reaction steps and low production cost

Inactive Publication Date: 2010-02-10
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above synthesis routes of methyl ethylamine all have the problem of being too long, in which the highly toxic dimethyl sulfate is used in the methylation

Method used

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  • Method for preparing ethylmethylamino formyl chloride
  • Method for preparing ethylmethylamino formyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) the preparation of methylethylamine:

[0028] Put 120ml of tetrahydrofuran and 120ml of toluene into a clean and dry 1000ml four-necked flask, cool it to 0°C with ice water, slowly add 156g of zinc chloride in batches, the heat release is violent, and after feeding, add N-methyl Add 60g of acetamide, drop it in about 30 minutes, then add 57.6g of potassium borohydride, and then stir for 30 minutes near 0°C, then remove the ice bath, stir at room temperature and naturally raise the temperature for 1 hour, then heat to 40°C and keep it for 1.5 hours. After the heat preservation is completed, slowly raise the temperature to reflux for 3 hours (in the heat preservation process, the method of gradually raising the temperature is adopted to let itself release heat and then heat up, which can effectively prevent the occurrence of material flushing and ensure the safety of the operation), after the heat preservation is completed, steam it out under normal pressure The solve...

Embodiment 2

[0032] (1) the preparation of methylethylamine:

[0033] Put 120ml of tetrahydrofuran and 120ml of benzene into a clean and dry 1000ml four-necked flask, cool it to 0°C with ice water, slowly add 156g of zinc chloride in batches, the heat release is violent, and after feeding, add N-methyl chloride dropwise at this temperature Add 60g of acetamide, drop it in about 30 minutes, then add 80g of potassium borohydride, and then stir for 30 minutes near 0°C, then remove the ice bath, stir at room temperature and naturally heat up for 1 hour, then heat to 40°C for 1.5 hours, keep warm After finishing, slowly heat up to reflux and keep warm for 3 hours. After the heat preservation is completed, about 120ml of the solvent is evaporated under normal pressure. After the evaporation is completed, the pH is adjusted to 2~3 with hydrochloric acid. The sodium oxide solution was used to adjust the pH to 14. After the adjustment, the temperature was raised again, and the liquid at 50-80° C. ...

Embodiment 3

[0037] (1) the preparation of methylethylamine:

[0038] Put 240ml of toluene into a clean and dry 1000ml four-necked flask, cool it to 0°C with ice water, slowly add 156g of zinc chloride in batches, the heat release is violent, after feeding, add 60g of N-ethylformamide dropwise at this temperature After dripping in about 30 minutes, add 46.8g of sodium borohydride, and then stir for 30 minutes near 0°C, then remove the ice bath, stir at room temperature and naturally raise the temperature for 1 hour, then heat to 40°C and keep it for 1.5 hours. Slowly heat up to reflux for 3 hours. After the heat preservation is completed, about 120ml of the solvent is evaporated under normal pressure. After the evaporation is completed, the pH is adjusted to 2~3 with hydrochloric acid. The potassium oxide solution was adjusted to pH=14. After the adjustment, the temperature was raised again, and the liquid at 50-80° C. was collected, which was methylethylamine, and 38 g of methylethylamine ...

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Abstract

The invention provides a method for preparing ethylmethylamino formyl chloride, which comprises the steps of: taking N-methylacetamide or N-ethylformamide as a raw material, performing a reduction reaction with a reducing agent and Lewis acid at a reflux temperature of an organic solvent (1) in the organic solvent (1) to obtain N-ethyl methyl amine, and reacting the N-ethyl methyl amine and triphosgene or phosgene to obtain the ethylmethylamino formyl chloride, wherein the organic solvent (1) is a mixed solution of methylbenzene, benzene and tetrahydrofuran or a mixed solution of the methylbenzene and the tetrahydrofuran; the reducing agent is KBH4, NaBH4, LiAlH4, Pd / C or an 45 percent BF3 / ether solution; the Lewis acid is one of zinc chloride, ferric trichloride or aluminum trichloride; and the molar ratio of the N-methylacetamide or the N-ethylformamide to the reducing agent to the Lewis acid is 1: 1.01-2.0: 1.01-1.8. The method has the advantages of easy reaction of the whole road,short road, raw and auxiliary material conservation, low production cost and the like, and is favorable for industrialized production.

Description

(1) Technical field [0001] The invention relates to a preparation method of ethylmethylcarbamoyl chloride. (2) Background technology [0002] Ethylmethylcarbamoyl chloride is a colorless transparent liquid, soluble in various organic solvents such as ether and dichloromethane. It can be used to synthesize rivastigmine tartrate, and rivastigmine tartrate is an effective drug used to alleviate the development of AD. Its mechanism of action is to inhibit acetylcholinesterase in the human brain and increase the content of acetylcholine in the central nervous system. The treatment of mild to moderate patients can effectively improve the memory of patients with less side effects. [0003] Ethylmethylcarbamoyl chloride, chemical name: N-ethylmethylcarbamoyl chloride, structural formula is as follows: [0004] [0005] As an important intermediate of rivastigmine tartrate, it has a very broad prospect. At present, it is reported in the literature that benzaldehyde is generally ...

Claims

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Application Information

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IPC IPC(8): C07C271/04C07C269/04
Inventor 徐建康郭永兵叶美其赵宗敏
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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