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Preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

A technology of ethylcarbodiimide hydrochloride and dimethylaminopropyl, applied in the field of preparation of 1--3-ethylcarbodiimide hydrochloride, can solve the problem of unsuitability for industrial production and low yield etc. to achieve high conversion rate, high total yield and simple operation

Active Publication Date: 2014-12-10
SHANDONG JINCHENG PHARMACEUTICAL GROUP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] This method yield is low, is not suitable for industrialized production

Method used

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  • Preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
  • Preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
  • Preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Weigh 12ml of carbon disulfide and dissolve it in 100ml of methanol, slowly add 20.4g of N,N'-dimethylpropylenediamine dropwise, control the temperature at 10-15°C, a white solid is formed during the dropping process, and the dropping is completed in 10-15 Incubate at °C for 1 hour, filter, and wash with methanol to obtain 38 g of white solid (Intermediate 1), with a yield of 95%.

[0048] Weigh 38g of the product from the previous step, add 120ml of chloroform, control the temperature at 10-15°C, add 24.2g of triethylamine, then slowly add 11.1g of ethyl chloroformate dropwise, dropwise for 1 hour, keep the temperature for 1 hour after the dropwise addition, until Dissolve, wash the organic phase, filter and dry to obtain the product (intermediate 2).

[0049] Weigh 12.9g of ethylamine (containing 70% water), add 60ml of chloroform, cool down to 10-15°C, slowly add intermediate 2 dropwise, keep warm for 1 hour after the dropwise addition, and wash the organic phase wit...

Embodiment 2

[0052] Weigh 24ml of carbon disulfide and dissolve it in 150ml of methanol, slowly add 43.8g of N,N'-dimethylpropylenediamine dropwise, control the temperature at 10-15°C, a white solid will form during the dropwise addition, and keep warm at 20°C after the dropwise addition After 2 hours, it was filtered and washed with methanol to obtain 75 g of white solid (Intermediate 1), with a yield of 96%.

[0053]Weigh 75g of the product from the previous step, add 200ml of dichloromethane, control the temperature at 10-15°C, add 45.8g of triethylamine, then slowly add 50.3g of ethyl chloroformate dropwise, dropwise for 2 hours, and keep warm for 1 hour after the dropwise addition , until dissolved, the organic phase was washed, filtered, and dried to obtain the product (intermediate 2).

[0054] Weigh 25.2g of ethylamine (containing 70% water), add 180ml of dichloromethane, cool down to 10-15°C, slowly add intermediate 2 dropwise, keep warm for 1 hour after the dropwise addition, and...

Embodiment 3

[0057] Weigh 24ml of carbon disulfide and dissolve it in 150ml of chloroform, slowly add 41.5g of N,N'-dimethylpropylenediamine dropwise, control the temperature at 10-15°C, keep the temperature at 15°C for 1 hour after the addition, and concentrate under reduced pressure to obtain White solid 72.4 g (Intermediate 1).

[0058] Add 180ml of chloroform to the white solid product 72.4 of the previous step, control the temperature at 10-15°C, add 41.2g of triethylamine, then slowly add 48.9g of ethyl chloroformate dropwise, dropwise for 2 hours, and keep warm for 1 hour after the dropwise addition is completed. To dissolve, wash the organic phase, filter, and dry to obtain the product (intermediate 2).

[0059] Weigh 26.2g of ethylamine (containing 70% of water), add 150ml of dichloromethane, cool down to 10-15°C, slowly add intermediate 2 dropwise, keep warm for 1 hour after the dropwise addition, and wash with lye with pH = 11-12 The organic phase was dried, reduced pressure, a...

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Abstract

The invention belongs to the field of organic chemical industry, and particularly relates to a preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The method comprises the following steps: enabling N,N'-dimethyl-1,3-propanediamine and carbon disulfide as raw materials to react in an organic solvent to generate an intermediate 1; enabling the intermediate 1 and ethyl chloroformate to react in the organic solvent, and preparing an intermediate 2 from triethylamine as an acid-binding agent; enabling the intermediate 2 and ethylamine to react in the organic solvent, so as to prepare an intermediate 3; adding a catalyst to the intermediate 3, oxidizing one time with an oxidant, so as to obtain a crude product 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, extracting and separating, so as to obtain an intermediate 4; and carrying out salt exchange reaction on the intermediate 4 and hydrochloride, so as to prepare the product 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The method has the advantages of relatively high conversion rate and relatively high total recovery rate and is simple to operate and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemical industry, in particular to a preparation method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. Background technique [0002] 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, referred to as EDC hydrochloride, molecular formula: C 8 h 17 N 3 HCl, the structural formula is: [0003] [0004] The relative molecular mass is 191.70, white crystalline powder, easy to absorb moisture, solubility in water >20g / 100ml, soluble in ethanol, melting point 110-114°C, used as an activating reagent for carboxyl groups in amide synthesis, and also for activating phosphate groups Groups, cross-linking of proteins and nucleic acids and preparation of immunoconjugates. The pH range when used is 4.0-6.0, and it is often used together with N-hydroxysuccinimide (NHS) or N-hydroxysulfosuccinimide to improve coupling efficiency. [0005] The preparation method of traditional 1-(3-dime...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C267/00
Inventor 郑庚修赵攀峰马晓芬宋倩
Owner SHANDONG JINCHENG PHARMACEUTICAL GROUP CO LTD
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